Pyrimidine derivatives, process and intermediate products for their preparation and pesticides or fungicides containing these derivatives

ABSTRACT

Pyrimidine compounds I                    
     wherein 
     X is C(CO 2 CH 3 )═NOCH 3 , C(CONHCH 3 )═NOCH 3 , C(CO 2 CH 3 )═CHOCH 3 , C(CO 2 CH 3 )═CHCH 3  or N(CO 2 CH 3 )—OCH 3 ; 
     R 1 , R 2  are hydrogen, alkyl, haloalkyl or alkoxy; 
     A is                    
     R 3  is hydrogen, alkyl, haloalkyl, phenoxyalkyl, cycloalkyl, cyano, alkoxy, hydroxyl or halogen; 
     R 4  is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, cycloalkyl or alkoxy; 
     Y is hydrogen, hydroxyl, halogen, optionally substituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio, 
     or their salt, their synthesis and intermediates therefore, and their activity against fungi or animal pests.

This application is a 371 of PCT/EP97/00423, filed Jan. 31, 1997.

The present invention relates to pyrimidine derivatives of the formula I

where the substituents have the following meanings:

X is C(CO₂CH₃)═NOCH₃, C(CONHCH₃)═NOCH₃, C(CO₂CH₃)═CHOCH₃,C(CO₂CH₃)═CHCH₃, N(CO₂CH₃)—OCH₃;

R¹ and R² independently of one another are hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxy;

A is

where the bond marked by * is to Y;

R³ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, phenoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkyl, cyano, C₁-C₄-alkoxy, hydroxyl, halogen;

R⁴ is hydrogen, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₁-C₆-cyanoalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₂-C₄-alkenyloxy-C₁-C₄-alkyl,C₁-C₄-halo-alkoxy-C₁-C₄-alkyl, C₁-C₄-oxoalkyl, C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy;

Y is hydrogen, hydroxyl, halogen, unsubstituted or substituted aryl,hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl, alkyl, alkenyl,alkynyl, haloalkyl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio,cycloalkyloxy or alkylthio,

where if X is C(CO₂CH₃)═CHOCH₃ A is not —O—,

or its salts.

Preferred compounds of the formula I, are those where the substituentshave the following meanings:

X is C(CO₂CH₃)═NOCH₃, C(CONHCH₃)═NOCH₃, C(CO₂CH₃)═CHOCH₃,C(CO₂CH₃)═CHCH₃, N(CO₂CH₃)—OCH₃;

R¹ and R² independently of one another are hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxy;

A is

where the bond marked by * is to Y;

R³ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, phenoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkyl, cyano, hydroxyl, halogen;

R⁴ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy;

Y is unsubstituted or substituted aryl, hetaryl, cycloalkyl,cycloalkenyl, heterocyclyl, alkyl, haloalkyl or alkoxy,

where if X is C(CO₂CH₃)═CHOCH₃ A is not —O—,

and their salts.

Especially preferred compounds of the formula 1 as claimed in claim 1are those where the substituent Y has the following meanings:

hydrogen, hydroxyl, halogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkyloxy, C₁-C₄-alkylthio, C₃-C₆-cycloalkyl,C₅-C₈-cycoalkenyl, heterocyclyl, aryl, aryloxy, arylthio,aryl-C₁-C₄-alkyl, aryl-C₂-C₄-alkenyl, aryloxy-C₁-C₄-alkyl,aryl-C₁-C₄-alkoxy, hetaryl, hetaryloxy, hetarylthio,hetaryl-C₁-C₄-alkyl, hetarylthio-C₁-C₄-alkyl, hetaryl-C₁-C₄-alkoxy orhetaryl-C₂-C₄-alkenyl, where the cyclic radicals can be partially orcompletely halogenated and/or can carry 1 to 3 of the following groups:

cyano, nitro, hydroxyl, mercapto, amino, formyl, carboxyl,aminocarbonyl, aminothiocarbonyl,

C₁-C₁₂-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkylsulfonyl,C₁-C₆-alkylsulfoxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyl,benzyloxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino,di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylamino,C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl,C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl,C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C(═NOR^(b))—Z_(n)—R^(c),NR^(f)—CO—D—R⁹, benzyl, benzyloxy, aryl, aryloxy, hetaryl or hetaryloxy,where the 6 last mentioned radicals can be partially or completelyhalogenated and/or can carry 1 to 3 of the following groups: cyano,C₁-C₆-alkyl, C₁-C₆-alkoxy-carbonyl, C₁-C₄-alkoxy, nitro,C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkyl, hydroxy, rhodano, formyl,aminocarbonylamino, methylsulfonylamino, aminocarbonyl,C₁-C₆-alkylaminocarbonyl;

Z is oxygen, sulfur or nitrogen, the nitrogen bearing hydrogen orC₁-C₆-alkyl;

D is a direct bond, oxygen or NR^(h);

n is 0 or 1;

R^(b) and R^(c) independently of one another are hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl or benzyl;

R^(f) is hydrogen, hydroxyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkoxy andC₁-C₆-alkoxycarbonyl;

R^(g) and R^(h) independently of one another are hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl , C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,aryl, aryl-C₁-C₆-alkyl, hetaryl or hetaryl-C₁-C₆-alkyl,

R⁹ hydrogen or C₁-C₆-alkyl.

Particulary preferred compounds are those where the substituent Y hasthe following meanings:

C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₃-C₆-cycloalkyl,C₅-C₈-cycoalkenyl, heterocyclyl, aryl or hetaryl, where the cyclicradicals can be partially or completely halogenated and/or can carry 1to 3 of the following groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl,C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylamino, C₁-C₆-alkylaminocarbonyl,di-C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylaminothiocarbonyl,di-C₁-C₆-alkylaminothiocarbonyl, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy,benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy,C(═NOR^(b))—Z_(n)—R^(c) or NR^(f)—CO—D—R⁹;

Z is oxygen, sulfur or nitrogen, the nitrogen bearing hydrogen orC₁-C₆-alkyl;

D is a direct bond, oxygen or NR^(h);

n is 0 or 1;

R^(b) and R^(c) independently of one another are hydrogen orC₁-C₆-alkyl;

R^(f) is hydrogen, hydroxyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkoxy andC₁-C₆-alkoxycarbonyl;

R^(g) and R^(h) independently of one another are hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,aryl, aryl-C₁-C₆-alkyl, hetaryl or hetaryl-C₁-C₆-alkyl.

The invention additionally relates to processes and intermediates forpreparing these compounds and to compositions comprising them forcontrolling animal pests and harmful fungi.

Phenylacetic acid derivatives for controlling pests are disclosed in theliterature (EP-A 422 597; EP-A 463 488; EP-A 370 629; EP-A 460 575; EP-A472 300; WO-A 90/07,493; WO-A 92/13,830; WO-A 92/18,487; WO-A 95/18,789;WO-A 95/21,153; WO-A 95/21,154; WO-A 95/21,156).

Pyrimidine derivatives for controlling pests are furthermore disclosedin the literature (EP-A 634 405).

It is an object of the present invention to provide novel compoundshaving an improved action.

We have found that this object is achieved by the pyrimidine derivativesI defined at the outset. We have additionally found processes andintermediates for their preparation and compositions comprising them forcontrolling animal pests and harmful fungi, and their use in thiscontext.

The compounds I are obtainable in various ways by methods known per sein the literature.

Fundamentally, it is insignificant in the synthesis of the compoundswhether the group X or the group Y—A— is synthesized first.

The synthesis of the group X is disclosed, for example, in theliterature cited at the outset and in EP-A 178 826, EP-A 493 711, EP-A534 216, EP-A 658 541, EP-A 658 542 and EP-A 658 543.

The novel pyrimidines of the formula I, where X is C(CO₂CH₃)═NOCH₃ orC(CONHCH₃)═N—OCH₃, are thus obtained, for example, by reacting anα-oxopyrimidinylacetic acid derivative of the formula IIa

where Y, A, R¹ and R² have the meanings indicated above, in a mannerknown per se (EP-A-493 711) with methoxyamine (CH₃O—NH₂) or methoxyaminehydrohalide, if appropriate in the presence of a diluent and ifappropriate in the presence of a reaction auxiliary(X═C(CO₂CH₃)═N—OCH₃), or by reacting the 2-oximinopyrimidinylacetic acidderivatives of the formula IIb

in a manner known per se (EP-A-477 631) with methylamine, if appropriatein the presence of a diluent and if appropriate in the presence of areaction auxiliary (X═C(CONHCH₃)═N—OCH₃).

Compounds of the general formula I where A, Y, R¹ and R² have themeanings indicated above, and X is C(CO₂CH₃)═CHOCH₃ or C(CO₂CH₃)═CH—CH₃,are obtained, for example, by reacting the compounds of the formula IIain a manner known per se (EP-A-513 580; Tetrahedron 3727 (1988); GB2172595) with a Wittig reagent of the formula IIc or IId.

Hal in the formulae IIc and IId is iodine, bromine, chlorine orfluorine, preferably iodine, bromine or chlorine; Ph is phenyl.

Alternatively, the pyrimidines of the formula I where X, Y, R¹ and R²have the meanings indicated and A is oxygen,

can also be obtained by reacting the halopyrimidine derivatives of theformula III

where Hal is bromine, chlorine or fluorine, preferably chlorine orfluorine, with nucleophiles of the formula Y—A—H (IIIa), where Y and Ahave the meanings indicated, if appropriate in the presence of a diluentand if appropriate in the presence of a reaction auxiliary.

Alternatively, the pyrimidines of the formula I where X, Y, R¹ and R²have the meanings indicated and A is

R³ and R⁴ having the meanings indicated above, can thus also be obtainedby reacting the halopyrimidine derivatives of the formula IV

in a similar manner to processes known from the literature (EP-A-513580; EP-A-400 417; DE-A-4 020 384; WO-A-95/21153), with nucleophiles ofthe formula Y—B—H (IVa) where Y has the meanings indicated and B is

R³ and R⁴ having the meanings indicated, if appropriate in the presenceof a diluent and if appropriate in the presence of a reaction auxiliary.Hal is iodine, bromine or chlorine, preferably bromine or chlorine.

Compounds of the general formula I where A, Y, R¹ and R² have themeanings indicated above and X is N(CO₂CH₃)—OCH₃ are obtained byconverting nitropyrimidine derivatives of the formula V

in a manner similar to processes known from the literature (WO 93/15046)into the corresponding methoxycarbamates of the formula I(X═N(CO₂CH₃)—OCH₃).

This is expediently carried out by first reducing a nitropyrimidinederivative of the formula V in a manner known per se to thecorresponding N-hydroxyaminopyrimidine of the formula X

and then reacting X with a carbonyl compound of the formula XIII

L¹—CO₂CH₃  XIII

where L¹ is a nucleophilically replaceable group, to give thepyrimidinecarbamate XIV

and then reacting XIV in a manner known per se with a reagent of theformula XV

CH₃—L²  XV

where L² is a nucleophilically replaceable group, with formation of thecompound I (X═N(CO₂CH₃)OCH₃).

L¹ and L² are, for example, halogen, e.g. chlorine, bromine or iodine,or alkyl- or arylsulfonate, e.g. methylsulfonate,trifluoromethylsulfonate, phenylsulfonate or methylphenylsulfonate.

The reduction of V to the hydroxylamine X is customarily carried out atfrom −30° C. to 80° C., preferably 0° C. to 60° C., in an inert organicsolvent in the presence of a catalyst [cf. Ann. Chem. 316, 278 (1901);EP-A 085 890; DE-A 19 50 27 00].

The reaction of the hydroxylamine X with XIII is customarily carried outat from −20° C. to 60° C., preferably 0° C. to 30° C., in an inertorganic solvent in the presence of a base [cf. WO-A 93/15046]. Thereaction of the pyrimidinecarbamate XIV with XV is customarily carriedout at from −20° C. to 80° C., preferably 0° C. to 60° C., in an inertorganic solvent in the presence of a base [cf. WO-A 93/15046].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, alcohols such as methanol, ethanol,n-propanol, isopropanol, n-butanol and tert-butanol, and dimethylsulfoxide and dimethylformamide, particularly preferably cyclohexane,toluene, methylene chloride, tert-butyl methyl ether and water. Mixturesof the solvents mentioned can also be used.

Suitable bases are generally inorganic compounds such as alkali metaland alkaline earth metal hydroxides such as lithium hydroxide, sodiumhydroxide, potassium hydroxide and calcium hydroxide, alkali metal andalkaline earth metal oxides such as lithium oxide, sodium oxide, calciumoxide and magnesium oxide, alkali metal and alkaline earth metalhydrides, such as lithium hydride, sodium hydride, potassium hydride andcalcium hydride, alkali metal amides such as lithium amide, sodium amideand potassium amide, alkali metal and alkaline earth metal carbonatessuch as lithium carbonate and calcium carbonate, and alkali metalhydrogen carbonates such as sodium hydrogen carbonate, organometalliccompounds, in particular alkali metal alkyls such as methyllithium,butyllithium and phenyllithium, alkylmagnesium halides such asmethylmagnesium chloride, and alkali metal and alkaline earth metalalkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide,potassium tert-butoxide and dimethoxymagnesium, additionally organicbases, e.g. tertiary amines such as trimethylamine, triethylamine,triisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine and 4-dimethylaminopyridine, andbicyclic amines. Potassium carbonate, sodium hydroxide and triethylamineare particularly preferred.

In generaly, the bases are employed in catalytic amounts, but they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

The starting compounds of the general formulae IIa, III, IV and V arestill unknown, and as novel substances are likewise a subject of thepresent application.

Novel compounds of the general formulae IIa, where Y, R¹ and R² have themeanings indicated above and A is oxygen, —C(R³)═NO— or

are obtained, for example, according to the following reaction scheme:

The pyrimidine derivatives of the formula VI are known from theliterature and/or can be prepared by processes known per se [J. Chem.Soc. 364 (1937); Chem. Pharm. Bull. 2354 (1971); JOC 2137 (1960); Chem.Ber. 803 (1962)]. Alkyl is expediently C₁-C₄-alkyl, such as, forexample, methyl, ethyl, or n-propyl. These can then be reacted withnucleophiles of the formula Y—A—H, where

Y has the meanings indicated above and

A is oxygen,

or with alkali metal salts of the formula Y—A—M, where M is expedientlysodium, potassium or lithium, if appropriate in the presence of areaction auxiliary, such as, for example, copper(I) chloride, and ifappropriate in the presence of a diluent.

Suitable diluents are, for example, aliphatic hydrocarbons such aspentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbonssuch as toluene, o-, m- and p-xylene, halogenated hydrocarbons such asmethylene chloride, chloroform and chlorobenzene, ethers such as diethylether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone, andtert-butyl methyl ketone, and also dimethyl sulfoxide anddimethylformamide, particularly preferably acetone, dimethylformamide,tetrahydrofuran and dimethyl sulfoxide. Mixtures of the solventsmentioned can also be used.

The process can also be carried out in a two-phase system, such as, forexample, water/toluene or water/dichloromethane, if appropriate in thepresence of a phase-transfer catalyst, such as, for example,tetrabutylammonium iodide, tetrabutylammonium bromide,tetrabutylammonium chloride, trimethylbenzylammonium chloride,15-crown-5, 18-crown-6 or tris[2-(2-methoxyethoxy)-ethyl]amine. Theprocess is preferably carried out in the presence of a suitableinorganic or organic base.

Suitable bases are generally inorganic compounds such as alkali metaland alkaline earth metal hydroxides such as lithium hydroxide, sodiumhydroxide, potassium hydroxide and calcium hydroxide, alkali metal andalkaline earth metal oxides such as lithium oxide, sodium oxide, calciumoxide and magnesium oxide, alkali metal and alkaline earth metalhydrides such as lithium hydride, sodium hydride, potassium hydride andcalcium hydride, alkali metal amides such as lithium amide, sodium amideand potassium amide, alkali metal and alkaline earth metal carbonatessuch as lithium carbonate and calcium carbonate, and alkali metalhydrogen carbonates such as sodium hydrogen carbonate, organometalliccompounds, in particular alkali metal alkyls such as methyllithium,butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride, and alkali metal and alkaline earth metal alkoxidessuch as sodium methoxide, sodium ethoxide, potassium ethoxide, potassiumtert-butoxide and dimethoxymagnesium, additionally organic bases, e.g.tertiary amines such as trimethylamine, triethylamine,triisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine and 4-dimethylaminopyridine, andbicyclic amines. Potassium carbonate, sodium hydroxide, triethylamineand sodium methoxide are particularly preferred.

In general, the bases are employed in catalytic amounts, but they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

When carrying out the process described above, the temperatures can bevaried within a wide range. In general, the process is carried out atfrom 0 to 150° C., preferably from 20 to 130° C.

The process is customarily carried out at normal pressure. However, itis also possible to work at elevated or reduced pressure.

To carry out the process described above, in general from 1.0 to 3.0mol, preferably 1.0 to 2.0 mol, of nucleophile Y—A—H and, if appropriatefrom 1.0 to 3.0 mol, preferably 1.0 to 2.0 mol, of reaction auxiliaryare employed per mole of VI.

The acid chlorides VIIa are expediently obtained from the compounds VIIby first hydrolyzing the carbalkoxy group of VII in a manner known perse in a first step and expediently converting the carboxylic acidobtained in a manner known per se into the acid chloride VIIa usingthionyl chloride (Houben-Weyl, Supplementary Volume 5, p. 225ff, p. 59ffand p. 604ff.).

The pyrimidinecarbonyl cyanides of the formula VIIb are obtained byreacting the acid chlorides of the formula VIIa with metal cyanides, forexample with copper(I) or sodium cyanide, if appropriate in the presenceof a diluent, such as, for example, acetonitrile, in a manner known perse, expediently at from 10 to 100° C. (EP-A-493 711).

The α-oxo-pyrimidinylacetic acid derivatives of the formula IIa areexpediently obtained by hydrolyzing the pyrimidinecarbonyl cyanides ofthe formula VIIb with aqueous acids, for example with hydrochloric acid,at from 10 to 100° C., then esterifying these by reaction with alcohols,for example methanol, if appropriate in the presence of a reactionauxiliary, such as, for example, sulfuric acid, and if appropriate inthe presence of diluents, such as, for example, toluene, at from 10 to150° C., analogously to known processes (EP-A-493 711).

Alternatively, α-oxo-pyrimidinylacetic acid derivatives of the formulaIIa are obtained by reacting β-ketosulfoxides of the formula VIIc with ahalogenating agent, for example N-bromosuccinimide, if appropriate inthe presence of a diluent, such as, for example, acetone, and thentreating in a manner known per se with an alcohol, such as, for example,methanol, at from 0 to 150° C. (EP-A-493 711).

Compounds of the general formula IIa where Y, R¹ and R² have themeanings indicated above, and A is —O—CH₂—, —C(R³)═NOCH₂— or

are obtained according to the following reaction scheme:

The pyrimidinecarboxylic acid esters of the formula VII, where Y and R¹have the meanings indicated above, A is —O—CH₂—, —C(R³)═NOCH₂— or

and R² is hydrogen, are obtained by reacting the dimethylaminomethylenederivatives of the formula VIIIb with amidines of the formulaR¹—C(NH₂)═NH or R¹—C(NH₂)═NH hydrohalide, if appropriate in the presenceof a diluent and if appropriate in the presence of a reaction auxiliary,in a manner similar to processes known from the literature[J.Heterocyclic Chem. 295 (1990); Farmaco, Ed. Sci. 48, 335 (1993);Heterocycles 1375 (1994)].

The dimethylaminomethylene derivatives of the formula VIIIb are known orcan be prepared by processes known from the literature [J. HeterocyclicChem. 21, 301 (1984)].

The acetoacetic ester derivatives of the formula VIIIa are also eitherknown or can be prepared by a process known per se [J. Chem. Soc. 529(1979)] if the halogen derivatives of the formula VIII, where Hal isbromine or chlorine, are reacted with nucleophiles of the formula Y—A—H,where Y has the meanings indicated above and

A is

The pyrimidinecarboxylic acid esters of the formula VII where Y and R¹have the meanings indicated above, A is —O—CH₂—, —C(R³)═NOCH₂— or

and R² is not hydrogen, are obtained by reacting the carbonylderivatives of the formula IXa with amidine derivatives of the formulaR¹—C(NH₂)═NH or R¹—C(NH₂)═NH hydrohalide, if appropriate in the presenceof a diluent and if appropriate in the presence of a reaction auxiliaryin a manner similar to processes known from the literature (J.Heterocyclic Chem. 27, 295 (1990)).

The carbonyl derivatives of the formula IXa are known or can be preparedby a process known per se [J. Heterocyclic Chem. 21, 301 (1984)] byreacting the β-keto esters of the formula IX with a carbonyl chloride ofthe formula Y—A—C—(C1)═O.

The further conversion of the pyrimidinecarboxylic acid esters of theformula VII into the α-oxo-pyrimidinyl acetic acid derivatives of theformula IIa, where Y, R¹ and R² have the meanings indicated above and Ais —O—CH₂—, —C(R³)═NOCH₂— or

is then carried out correspondingly as described for scheme 1.

The nitropyrimidine derivatives of the formula V, where Y, R¹ and R²have the meanings indicated above and A is oxygen, —C(R³)═NO— or

are obtained according to the following reaction scheme:

The nitropyrimidine derivatives of the formula V, where Y, R¹ and R²have the meanings indicated above and A is oxygen, —C(R³)═NO— or

can be prepared from the halopyrimidine derivatives of the formula XIcaccording to processes known per se by reacting these with nucleophilesof the formula Y—A—H, where Y has the meanings indicated above and A isoxygen, —C(R³)═NO— or

or with alkali metal salts of the formula Y—A—M, where M is sodium,potassium or lithium, if appropriate in the presence of a reactionauxiliary, such as, for example, copper(I) chloride, and if appropriatein the presence of a diluent.

Suitable diluents are, for example, aliphatic hydrocarbons such aspentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbonssuch as toluene, o-, m- and p-xylene, halogenated hydrocarbons such asmethylene chloride, chloroform and chlorobenzene, ethers such as diethylether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide anddimethylformamide, particularly preferably tetrahydrofuran, acetone,dimethylformamide, acetonitrile and dimethyl sulfoxide. Mixtures of thesolvents mentioned can also be used.

The process can also be carried out in a two-phase system, such as, forexample, water/toluene or water/dichloromethane, if appropriate in thepresence of a phase-transfer catalyst, such as, for example,tetrabutylammonium iodide, tetrabutylammonium bromide,tetrabutylammonium chloride, trimethylbenzylammonium chloride,15-crown-5, 18-crown-6 or tris[2-(2-methoxyethoxy)-ethyl]amine. Theprocess is preferably carried out in the presence of a suitableinorganic or organic base.

Suitable bases are generally inorganic compounds such as alkali metaland alkaline earth metal hydroxides such as lithium hydroxide, sodiumhydroxide, potassium hydroxide and calcium hydroxide, alkali metal andalkaline earth metal oxides such as lithium oxide, sodium oxide, calciumoxide and magnesium oxide, alkali metal and alkaline earth metalhydrides such as lithium hydride, sodium hydride, potassium hydride andcalcium hydride, alkali metal amides such as lithium amide, sodium amideand potassium amide, alkali metal and alkaline earth metal carbonatessuch as lithium carbonate and calcium carbonate, and alkali metalhydrogen carbonates such as sodium hydrogen carbonate, organometalliccompounds, in particular alkali metal alkyls such as methyllithium,butyllithium and phenyllithium, alkylmagnesium halides such asmethylmagnesium chloride, and alkali metal and alkaline earth metalalkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide,potassium tert-butoxide and dimethoxymagnesium, additionally organicbases, e.g. tertiary amines such as trimethylamine, triethylamine,triisopropylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine and 4-dimethylaminopyridine, andbicyclic amines. Potassium carbonate, sodium hydroxide, triethylamineand sodium methoxide are particularly preferred.

In general, the bases are employed in catalytic amounts, but they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

When carrying out the process described above, the temperatures can bevaried within a wide range. In general, the process is carried out atfrom 0 to 150° C., preferably from 20 to 130° C.

The process is customarily carried out at normal pressure. However, itis also possible to work at elevated or reduced pressure.

To carry out the process described above, in general from 1.0 to 3.0mol, preferably 1.0 to 2.0 mol, of nucleophile Y—A—H and, ifappropriate, from 1.0 to 3.0 mol, preferably 1.0 to 2.0 mol, of reactionauxiliary are employed per mole of XIc.

The reaction is carried out and worked up and the products are isolatedaccording to methods known per se.

The halopyrimidine derivatives of the formula XIc where R¹ and R² havethe meanings indicated above can be prepared from the correspondinghydroxypyrimidine derivatives of the formula XIb according to a processknown per se, e.g. by reaction with POCl₃.

The hydroxypyrimidine derivatives of the formula XIb are either known orcan be prepared from the compounds of the formula XIa by reaction withamidines of the formula R¹—C(NH₂)═NH or R¹—C(NH₂)═NH hydrohalide, ifappropriate in the presence of a diluent and if appropriate in thepresence of a reaction auxiliary in a manner similar to processes knownfrom the literature [Khim. Farm. Zh, 25 (9) 62 (1991)].

The nitropyrimidine derivatives of the formula V, where Y, R¹ and R²have the meanings indicated above and A is —O—CH₂—, —C(R³)═NOCH₂— or

are obtained according to the following reaction scheme:

The nitropyrimidine derivatives of the formula V, where Y, R¹ and R²have the meanings indicated above and A is —O—CH₂—, —C(R³)═NOCH₂— or

can be prepared from the dimethylaminomethylene derivatives of theformula XIIb according to a process known per se by reacting these withamidine derivatives of the formula R¹—C(NH₂)═NH or R¹—C(NH₂)═NHhydrohalide, if appropriate in the presence of a diluent and ifappropriate in the presence of a reaction auxiliary, in a manner similarto processes known from the literature (J. Heterocyclic Chem. 27, 295(1990)).

The dimethylaminomethylene derivatives of the formula XIIb can beprepared from the halonitro derivatives of the formula XII which areknown or accessible by processes known per se, Hal in the formula XIIexpediently being bromine or chlorine, by reaction with nucleophiles ofthe formula Y—A—H where Y has the meanings indicated above and

or by reaction with alkali metal salts of the formula Y—A—M, where M issodium, potassium or lithium, if appropriate in the presence of areaction auxiliary, such as, for example, copper(I) chloride, and ifappropriate in the presence of a diluent.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and dimethyl sulfoxide and dimethylformamide,particularly preferably tetrahydrofuran, acetone, dimethylformamide,acetonitrile and dimethyl sulfoxide. Mixtures of the solvents mentionedcan also be used.

The process can also be carried out in a two-phase system, such as, forexample, water/toluene or water/dichloromethane, if appropriate in thepresence of a phase-transfer catalyst, such as, for example,tetrabutylammonium chloride, 15-crown-5, 18-crown-6 ortris[2-(2-methoxyethoxy)ethyl]amine. The process is preferably carriedout in the presence of a suitable inorganic or organic base.

Suitable bases are generally inorganic compounds such as alkali metaland alkaline earth metal hydroxides such as lithium hydroxide, sodiumhydroxide, potassium hydroxide and calcium hydroxide, alkali metal andalkaline earth metal oxides such as lithium oxide, sodium oxide, calciumoxide and magnesium oxide, alkali metal and alkaline earth metalhydrides such as lithium hydride, sodium hydride, potassium hydride andcalcium hydride, alkali metal amides such as lithium amide, sodium amideand potassium amide, alkali metal and alkaline earth metal carbonatessuch as lithium carbonate and calcium carbonate, and alkali metalhydrogen carbonates such as sodium hydrogen carbonate, organometalliccompounds, in particular alkali metal alkyls such as methyl lithium,butyl lithium and phenyl lithium, alkylmagnesium halides such asmethylmagnesium chloride, and alkali metal and alkaline earth metalalkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide,potassium tert-butoxide and dimethoxymagnesium, additionally organicbases, e.g. tertiary amines such as trimethylamine, triethylamine,triisopropylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine and 4-dimethylaminopyridine, andbicyclic amines. Potassium carbonate, sodium hydroxide, triethylamineand sodium methoxide are particularly preferred.

In general, the bases are employed in catalytic amounts, but they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

When carrying out the process described above, the temperatures can bevaried within a wide range. In general, the process is carried out atfrom 0 to 150° C., preferably from 20 to 130° C.

The process is customarily carried out at normal pressure. However, itis also possible to work at elevated or reduced pressure.

To carry out the process described above, in general from 1.0 to 3.0mol, preferably 1.0 to 2.0 mol, of nucleophile Y—A—H and, ifappropriate, from 1.0 to 3.0 mol, preferably 1.0 to 2.0 mol, of reactionauxiliary are employed per mole of XIIa. The reaction is carried out andworked up and the products are isolated by methods known per se.

The compounds of the formula XIIa can then be converted according to aprocess known per se into the dimethylaminomethylene derivatives of theformula XIIb (1. Chem. Ber. 1081 (65), 2. Chem. Ber. 3407 (64), 3.Synth. Communications 939 (82)).

On account of their C═C and C═N double bonds, the compounds I can beobtained as E/Z isomer mixtures which can be separated into theindividual compounds in a customary manner, for example bycrystallization or chromatography.

If isomer mixtures are obtained in the synthesis, in general, however, aseparation is not absolutely necessary, as the individual isomers arepartially converted into one another during preparation for use or inuse (e.g. under the action of light, acid or base). Correspondingconversions can also take place after use, for example in the treatmentof plants, in the treated plant or in the harmful fungus or animal pestto be controlled.

With regard to the C═N and C═C double bond of the substituents X, the Eisomers of the compounds I are preferred with respect to their activity(configuration based on the OCH₃ or CH₃ group in relation to the CO₂CH₃or CONHCH₃ group).

With regard to the —N═CR³—CY═N double bonds, in general the cis-isomersof the compounds I (configuration based on the radical R³ or Y inrelation to the —OCH₂ or —OR⁴ group) are preferred with respect to theiractivity.

In the definitions of the compounds I indicated at the outset,collective terms were used which are generally representative of thefollowing groups:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: straight-chain or branched alkyl groups having 1 to 4, 6 or 10carbon atoms, e.g. C₁-C₆-alkyl such as methyl, ethyl, propyl,1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl,pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-l-methylpropyl and 1-ethyl-2-methylpropyl;

alkylamino: an amino group which carries a straight-chain or branchedalkyl group having 1 to 6 carbon atoms as mentioned above;

dialkylamino: an amino group which carries two straight-chain orbranched alkyl groups which are independent of one another and each have1 to 6 carbon atoms as mentioned above;

alkylcarbonyl: straight-chain or branched alkyl groups having 1 to 10carbon atoms, which are bonded to the structure via a carbonyl group(—CO—);

alkylsulfonyl: straight-chain or branched alkyl groups having 1 to 6 or10 carbon atoms, which are bonded to the structure via a sulfonyl group(—SO₂—);

alkylsulfoxyl: straight-chain or branched alkyl groups having 1 to 6carbon atoms, which are bonded to the structure via a sulfoxyl group(—S(═O)—);

alkylaminocarbonyl: Alkylamino groups having 1 to 6 carbon atoms asmentioned above, which are bonded to the structure via a carbonyl group(—CO—);

dialkylaminocarbonyl: dialkylamino groups each having 1 to 6 carbonatoms per alkyl radical as mentioned above, which are bonded to thestructure via a carbonyl group (—CO—);

alkylaminothiocarbonyl: alkylamino groups having 1 to 6 carbon atoms asmentioned above, which are bonded to the structure via a thiocarbonylgroup (—CS—);

dialkylaminothiocarbonyl: dialkylamino groups each having 1 to 6 carbonatoms per alkyl radical as mentioned above, which are bonded to thestructure via a thiocarbonyl group (—CS—);

haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbonatoms, it being possible in these groups for the hydrogen atoms to bepartially or completely replaced by halogen atoms as mentioned above,eg. C₁-C₂-haloalkyl such as chloromethyl, dichloromethyl,trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

alkoxy: straight-chain or branched alkyl groups having 1 to 4 or 6carbon atoms as mentioned above, which are bonded to the structure viaan oxygen atom (—O—), eg. C₁-C₆-alkoxy such as methoxy, ethoxy, propoxy,1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy,1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy,3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy,2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyand 1-ethyl-2-methylpropoxy; alkoxycarbonyl: straight-chain or branchedalkyl groups having 1 to 6 carbon atoms, which are bonded to thestructure via an oxycarbonyl group (—OC(═O)—);

haloalkoxy: straight-chain or branched alkyl groups having 1 to 6 carbonatoms, it being possible in these groups for the hydrogen atoms to bepartially or completely replaced by halogen atoms as mentioned above,and these groups being bonded to the structure via an oxygen atom;

alkylthio: straight-chain or branched alkyl groups having 1 to 4 or 6carbon atoms as mentioned above, which are bonded to the structure via asulfur atom (—S—), eg. C₁-C₆-alkylthio such as methylthio, ethylthio,propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,2-methylpropylthio, 1,1-dimethylethylthio, pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and1-ethyl-2-methylpropylthio;

cycloalkyl: monocyclic alkyl groups having 3 to 6 carbon ring members,eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

alkenyl: straight-chain or branched alkenyl groups having 2 to 6 or 10carbon atoms and a double bond in any desired position, eg.C₂-C₆-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl,1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl,1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl,2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl,2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl,1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl,5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl,3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl,2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl,4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl,1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl,1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl,3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl,1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl,2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl,1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and1-ethyl-2-methyl-2-propenyl;

alkenyloxy: sraight-chain or branched alkenyl groups having 2 to 6carbon atoms and a double bond in any desired position, which are bondedto the structure via an oxygen atom (—O—);

alkenylthio and alkenylamino: straight-chain or branched alkenyl groupshaving 2 to 6 carbon atoms and a double bond in any desired position,which (alkenylthio) are bonded to the structure via a sulfur atom or(alkenylamino) a nitrogen atom.

alkenylcarbonyl: straight-chain or branched alkenyl groups having 2 to10 carbon atoms and a double bond in any desired position, which arebonded to the structure via a carbonyl group (—CO—);

alkynyl: straight-chain or branched akynyl groups having 2 to 10 carbonatoms and a triple bond in any desired position, eg. C₂-C₆-alkynyl suchas ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl,2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl,1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

alkynyloxy or alkynylthio and alkynylamino: straight-chain or branchedalkynyl groups having 2 to 6 carbon atoms and a triple bond in anydesired position, which (alkynyloxy) are bonded to the structure via anoxygen atom or (alkynylthio) via a sulfur atom or (alkynylamino) via anitrogen atom.

alkynylcarbonyl: straight chain or branched alkynyl groups having 3 to10 carbon atoms and a triple bond in any desired position, which arebonded to the structure via a carbonyl group (—CO—);

cycloalkenyl and cycloalkenyloxy, cycloalkenylthio andcycloalkenylamino: monocyclic alkenyl groups having 3 to 6 carbon ringmembers, which are bonded to the structure directly or (cycloalkenyloxy)via an oxygen atom or (cycloalkenylthio) a sulfur atom or(cycloalkenylamino) via a nitrogen atom, eg. cyclopropenyl,cyclobutenyl, cyclopentenyl or cyclohexenyl.

cycloalkoxy or cycloalkylthio and cycloalkylamino: monocyclic alkenylgroups having 3 to 6 carbon ring members, which (cycloalkoxy) are bondedto the structure via an oxygen atom or (cycloalkylthio) a sulfur atom or(cycloalkylamino) via a nitrogen atom, eg. cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl;

heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclylamino:three- to six-membered, saturated or partially unsaturated mono- orpolycyclic heterocycles, which contain 1 to 3 hetero atoms selected froma group consisting of oxygen, nitrogen and sulfur, and which are bondedto the structure directly or (heterocyclyloxy) via an oxygen atom or(heterocyclylthio) via a sulfur atom or (heterocyclylamino) via anitrogen atom, such as, for example, 2-tetrahydrofuranyl, oxiranyl,3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl,2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,2,3-dihydrofur-3-yl, 2,3-dihydrofur-4-yl, 2,3-dihydrofur-5-yl,2,5-dihydro-fur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl,2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl,2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl,2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl,2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl,2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl,4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl,2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl,2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyrazol-3-yl,2,3-dihydroisopyrazol-4-yl, 2,3-dihydroisopyrazol-5-yl,4,5-dihydroisopyrazol-3-yl, 4,5-dihydroisopyrazol-4-yl,4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3-yl,2,5-dihydroisopyrazol-4-yl, 2,5-dihydroisopyrazol-5-yl,2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl,4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl,2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl,2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl,2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl,4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl,2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl,2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl,2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl,4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl,4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl,2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl,3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl,3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl,2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl,5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl,1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl,1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl,1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl,4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl,2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl,1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl;

aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono-or polycyclic hydrocarbon radicals which are bonded to the structuredirectly or (aryloxy) via an oxygen atom (—O—) or g(arylthio) a sulfuratom (—S—), (arylcarbonyl) via a carbonyl group (—CO—) or (arylsulfonyl)via a sulfonyl group (—SO₂—), eg. phenyl, naphthyl and phenanthrenyl orphenoxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyland sulfonyl radicals;

arylamino: aromatic mono- or polycyclic hydrocarbon radicals which arebonded to the structure via a nitrogen atom;

hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl:aromatic mono- or polycyclic radicals which, beside carbon ring members,additionally can contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atomsand an oxygen atom or a sulfur atom or an oxygen atom or a sulfur atomand which are bonded to the structure directly or (hetaryloxy) via anoxygen atom (—O—) or (hetarylthio) a sulfur atom (—S—),(hetarylcarbonyl) via a carbonyl group (—CO—) or (hetarylsulfonyl) via asulfonyl group (SO₂—), eg.

5-membered heteroaryl, comprising one to three nitrogen atoms:5-membered ring heteroaryl groups which, beside carbon atoms, cancontain one to three nitrogen atoms as ring members, eg. 2-pyrrolyl,3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl,4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;

5-membered heteroaryl, comprising one to four nitrogen atoms or one tothree nitrogen atoms and a sulfur or oxygen atom or an oxygen or asulfur atom: 5-membered ring heteroaryl groups which, beside carbonatoms, can contain one to four nitrogen atoms or one to three nitrogenatoms and a sulfur or oxygen atom or an oxygen or sulfur atom as ringmembers, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl,3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,1,3,4-triazol-2-yl;

benzo-fused 5-membered heteroaryl, comprising one to three nitrogenatoms or a nitrogen atom and/or an oxygen or sulfur atom: 5-memberedring heteroaryl groups which, beside carbon atoms, can contain one tofour nitrogen atoms or one to three nitrogen atoms and a sulfur oroxygen atom or an oxygen or a sulfur atom as ring members, and in whichtwo adjacent carbon ring members or a nitrogen and an adjacent carbonring member can be bridged by a buta-1,3-diene-1,4-diyl group;

5-membered heteroaryl bonded via nitrogen, comprising one to fournitrogen atoms, or benzo-fused 5-membered heteroaryl bonded vianitrogen, comprising one to three nitrogen atoms: 5-membered ringhetaryl groups which, beside carbon atoms, can contain one to fournitrogen atoms or one to three nitrogen atoms as ring members, and inwhich two adjacent carbon ring members or a nitrogen and an adjacentcarbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group,these rings being bonded to the structure via one of the nitrogen ringmembers;

6-membered heteroaryl. comprising one to three or one to four nitrogenatoms: 6-membered ring heteroaryl groups which, beside carbon atoms, cancontain one to three or one to four nitrogen atoms as ring members, eg.2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;

benzo-fused 6-membered heteroaryl, comprising one to four nitrogenatoms: 6-membered ring heteroaryl groups in which two adjacent carbonring members can be bridged by a buta-1,3-dien-1,4-diyl group, eg.quinoline, isoquinoline, quinazoline and quinoxaline,

pyrido[3,2-d]thiazol-2-yl,

or the corresponding oxy, thio, carbonyl or sulfonyl groups;

hetarylamino: aromatic mono- or polycyclic radicals which, beside carbonring members, can additionally contain one to four nitrogen atoms or oneto three nitrogen atoms and an oxygen or a sulfur atom and which arebonded to the structure via a nitrogen atom.

The term partially or completely halogenated is intended to express thatin the groups characterized in this way the hydrogen atoms are partiallyor completely replaced by identical or different halogen atoms asmentioned above.

The term unsubstituted or substituted is intended to express that in thegroups characterized in this way the hydrogen atoms are partially orcompletely replaced by identical or different groups, for example groupsof the type which are mentioned under the collective terms detailedabove.

With respect to their biological action, compounds of the formula I arepreferred where R¹ is methyl and R² is hydrogen.

Compounds I are additionally preferred where R¹ is hydrogen and R² ismethyl.

Compounds I are furthermore preferred where R¹ is trifluoromethyl and R²is hydrogen.

In addition, compounds I are preferred where R¹ is hydrogen and R² istrifluoromethyl.

Equally, compounds I are preferred where R¹ and R² are hydrogen.

Compounds I are particularly preferred where X is C(CONHCH₃)═NOCH₃.

Additionally, compounds I are preferred where X is C(CO₂CH₃)═NOCH₃.

Equally, compounds I are preferred where X is C(CO₂CH₃)═CHOCH₃.

In addition, compounds I are particularly preferred where X isC(CO₂CH₃)═CHCH₃.

Furthermore, compounds I are preferred where X is N(CO₂CH₃)—OCH₃.

Additionally, compounds I are particularly preferred where A is —OCH₂—.

Equally, compounds I are particularly preferred where A is—C(R³)═NOCH₂—.

In additiion, compounds I are particularly preferred where A is

Furthermore, compounds I are preferred where A is —O—.

Equally, compounds I are particularly preferred where A is —C(R³)═N—O—.

Furthermore, compounds I are particularly preferred where A is

Additionally, compounds I are particularly preferred where R³ isC₁-C₄-alkyl, in particular methyl.

Equally, particularly preferred compounds I are those where R³ istrifluoromethyl.

In addition, compounds I are particularly preferred where R³ iscyclopropyl.

Furthermore, compounds I are particularly preferred where R³ isC₁-C₄-alkoxy, in particular methoxy.

In particular, compounds I are also preferred where Y is aryl, inparticular unsubst. or subst. phenyl.

Additionally, compounds I are particularly preferred where Y iscycloalkyl, in particular cyclohexyl.

Additionally, compounds I are particularly preferred where Y is hetaryl,in particular unsubst. or subst. thienyl, isoxazolyl, pyrazolyl,pyridinyl and pyrimidinyl.

In particular, compounds I are also preferred where R⁴ is C₁-C₄-alkyl,in particular methyl or ethyl.

Additionally, compounds I are particularly preferred where R⁴ isC₃-C₄-alkenyl, in particular allyl.

Equally, particularly preferred compounds I are those where R⁴ isC₃-C₄-alkynyl, in particular propargyl.

Furthermore, particularly preferred compounds I are those where R⁴ ishaloalkenyl, in particular trans-chloroallyl.

Table 1

Compounds of the general formula IA.1, where Y for a compound in eachcase corresponds to one line of Table B

Table 2

Compounds of the general formula IA.2 where Y for a compound in eachcase corresponds to one line of Table B

Table 3

Compounds of the general formula IA.3 where Y for a compound in eachcase corresponds to one line of Table B

Table 4

Compounds of the general formula IA.4 where Y for a compound in eachcase corresponds to one line of Table B

Table 5

Compounds of the general formula IA.5 where Y for a compound in eachcase corresponds to one line of Table B

Table 6

Compounds of the general formula IA.6 where Y for a compound in eachcase corresponds to one line of Table B

Table 7

Compounds of the general formula IA.7 where Y for a compound in eachcase corresponds to one line of Table B

Table 8

Compounds of the general formula IA.8 where Y for a compound in eachcase corresponds to one line of Table B

Table 9

Compounds of the general formula IA.9 where Y for a compound in eachcase corresponds to one line of Table B

Table 10

Compounds of the general formula IA.10 where Y for a compound in eachcase corresponds to one line of Table B

Table 11

Compounds of the general formula IA.11 where Y for a compound in eachcase corresponds to one line of Table B

Table 12

Compounds of the general formula IA.12 where Y for a compound in eachcase corresponds to one line of Table B

Table 13

Compounds of the general formula IA.13 where Y for a compound in eachcase corresponds to one line of Table B

Table 14

Compounds of the general formula IA.14 where Y for a compound in eachcase corresponds to one line of Table B

Table 15

Compounds of the general formula IA.15 where Y for a compound in eachcase corresponds to one line of Table B

Table 16

Compounds of the general formula IA.16 where Y for a compound in eachcase corresponds to one line of Table B

Table 17

Compounds of the general formula IA.17 where Y for a compound in eachcase corresponds to one line of Table A

Table 18

Compounds of the general formula IA.18 where Y for a compound in eachcase corresponds to one line of Table A

Table 19

Compounds of the general formula IA.19 where Y for a compound in eachcase corresponds to one line of Table A

Table 20

Compounds of the general formula IA.20 where Y for a compound in eachcase corresponds to one line of Table A

Table 21

Compounds of the general formula IA.21 where Y for a compound in eachcase corresponds to one line of Table A

Table 22

Compounds of the general formula IA.22 where Y for a compound in eachcase corresponds to one line of Table A

Table 23

Compounds of the general formula IA.23 where Y for a compound in eachcase corresponds to one line of Table A

Table 24

Compounds of the general formula IA.24 where Y for a compound in eachcase corresponds to one line of Table A

Table 25

Compounds of the general formula IA.25 where Y for a compound in eachcase corresponds to one line of Table A

Table 26

Compounds of the general formula IA.26 where Y for a compound in eachcase corresponds to one line of Table A

Table 27

Compounds of the general formula IA.27 where Y for a compound in eachcase corresponds to one line of Table A

Table 28

Compounds of the general formula IA.28 where Y for a compound in eachcase corresponds to one line of Table A

Table 29

Compounds of the general formula IA.29 where Y for a compound in eachcase corresponds to one line of Table A

Table 30

Compounds of the general formula IA.30 where Y for a compound in eachcase corresponds to one line of Table A

Table 31

Compounds of the general formula IA.31 where Y for a compound in eachcase corresponds to one line of Table A

Table 32

Compounds of the general formula IA.32 where Y for a compound in eachcase corresponds to one line of Table A

Table 33

Compounds of the general formula IA.33 where Y for a compound in eachcase corresponds to one line of Table A

Table 34

Compounds of the general formula IA.34 where Y for a compound in eachcase corresponds to one line of Table A

Table 35

Compounds of the general formula IA.35 where Y for a compound in eachcase corresponds to one line of Table A

Table 36

Compounds of the general formula IA.36 where Y for a compound in eachcase corresponds to one line of Table A

Table 37

Compounds of the general formula IA.37 where Y for a compound in eachcase corresponds to one line of Table C

Table 38

Compounds of the general formula IA.38 where Y for a compound in eachcase corresponds to one line of Table C

Table 39

Compounds of the general formula IA.39 where Y for a compound in eachcase corresponds to one line of Table C

Table 40

Compounds of the general formula IA.40 where Y for a compound in eachcase corresponds to one line of Table C

Table 41

Compounds of the general formula IA.41 where Y for a compound in eachcase corresponds to one line of Table C

Table 42

Compounds of the general formula IA.42 where Y for a compound in eachcase corresponds to one line of Table C

Table 43

Compounds of the general formula IA.43 where Y for a compound in eachcase corresponds to one line of Table C

Table 44

Compounds of the general formula IA.44 where Y for a compound in eachcase corresponds to one line of Table C

Table 45

Compounds of the general formula IA.45 where Y for a compound in eachcase corresponds to one line of Table C

Table 46

Compounds of the general formula IA.46 where Y for a compound in eachcase corresponds to one line of Table C

Table 47

Compounds of the general formula IA.47 where Y for a compound in eachcase corresponds to one line of Table C

Table 48

Compounds of the general formula IA.48 where Y for a compound in eachcase corresponds to one line of Table C

Table 49

Compounds of the general formula IA.49 where Y for a compound in eachcase corresponds to one line of Table C

Table 50

Compounds of the general formula IA.50 where Y for a compound in eachcase corresponds to one line of Table C

Table 51

Compounds of the general formula IA.51 where Y for a compound in eachcase corresponds to one line of Table C

Table 52

Compounds of the general formula IA.52 where Y for a compound in eachcase corresponds to one line of Table C

Table 53

Compounds of the general formula IA.53 where Y for a compound in eachcase corresponds to one line of Table C

Table 54

Compounds of the general formula IA.54 where Y for a compound in eachcase corresponds to one line of Table C

Table 55

Compounds of the general formula IA.55 where Y for a compound in eachcase corresponds to one line of Table C

Table 56

Compounds of the general formula IA.56 where Y for a compound in eachcase corresponds to one line of Table C

Table 57

Compounds of the general formula IA.57 where Y and R⁴ for a compound ineach case correspond to one line of Table D

Table 58

Compounds of the general formula IA.58 where Y and R⁴ for a compound ineach case correspond to one line of Table D

Table 59

Compounds of the general formula IA.59 where Y and R⁴ for a compound ineach case correspond to one line of Table D

Table 60

Compounds of the general formula IA.60 where Y and R⁴ for a compound ineach case correspond to one line of Table D

Table 61

Compounds of the general formula IA.61 where Y and R4 for a compound ineach case correspond to one line of Table D

Table 62

Compounds of the general formula IA.62 where Y for a compound in eachcase corresponds to one line of Table C

Table 63

Compounds of the general formula IA.63 where Y for a compound in eachcase corresponds to one line of Table C

Table 64

Compounds of the general formula IA.64 where Y for a compound in eachcase corresponds to one line of Table A

Table 65

Compounds of the general formula IA.65 where Y for a compound in eachcase corresponds to one line of Table A

Table 66

Compounds of the general formula IA.66 where Y for a compound in eachcase corresponds to one line of Table C

Table 67

Compounds of the general formula IA.67 where Y for a compound in eachcase corresponds to one line of Table C

Table 68

Compounds of the general formula IA.68 where Y for a compound in eachcase corresponds to one line of Table C

Table 69

Compounds of the general formula IA.69 where Y for a compound in eachcase corresponds to one line of Table C

Table 70

Compounds of the general formula IA.70 where Y for a compound in eachcase corresponds to one line of Table C

Table 71

Compounds of the general formula IA.71 where Y for a compound in eachcase corresponds to one line of Table C

Table 72

Compounds of the general formula IA.72 where Y for a compound in eachcase corresponds to one line of Table C

Table 73

Compounds of the general formula IA.73 where Y for a compound in eachcase corresponds to one line of Table C

Table 74

Compounds of the general formula IA.74 where Y for a compound in eachcase corresponds to one line of Table C

Table 75

Compounds of the general formula IA.75 where Y for a compound in eachcase corresponds to one line of Table C

Table 76

Compounds of the general formula IA.76 where Y for a compound in eachcase corresponds to one line of Table C

Table 77

Compounds of the general formula IA.77 where Y for a compound in eachcase corresponds to one line of Table C

Table 78

Compounds of the general formula IA.78 where Y for a compound in eachcase corresponds to one line of Table C

Table 79

Compounds of the general formula IA.79 where Y for a compound in eachcase corresponds to one line of Table C

Table 80

Compounds of the general formula IA.80 where Y for a compound in eachcase corresponds to one line of Table C

Table 81

Compounds of the general formula IA.81 where Y for a compound in eachcase corresponds to one line of Table C

Table 82

Compounds of the general formula IA.82 where Y for a compound in eachcase corresponds to one line of Table D

Table 83

Compounds of the general formula IA.83 where Y and R⁴ for a compound ineach case correspond to one line of Table D

Table 84

Compounds of the general formula IA.84 where Y and R⁴ for a compound ineach case correspond to one line of Table D

Table 85

Compounds of the general formula IA.85 where Y and R⁴ for a compound ineach case correspond to one line of Table D

Table 86

Compounds of the general formula IA.86 where Y and R⁴ for a compound ineach case correspond to one line of Table D

Table 87

Compounds of the general formula IA.87 where Y for a compound in eachcase corresponds to one line of Table E

Table 88

Compounds of the general formula IA.88 where Y for a compound in eachcase corresponds to one line of Table E

Table 89

Compounds of the general formula IA.89 where Y for a compound in eachcase corresponds to one line of Table E

Table 90

Compounds of the general formula IA.90 where Y for a compound in eachcase corresponds to one line of Table E

Table 91

Compounds of the general formula IA.91 where the substitution patterncorresponds to the radicals of Table F

TABLE A A.1 C₆H₅ A.2 2-F—C₆H₄ A.3 3-F—C₆H₄ A.4 4-F—C₆H₄ A.5 2-Cl—C₆H₄A.6 3-Cl—C₆H₄ A.7 4-Cl—C₆H₄ A.8 2-CH₃—C₆H₄ A.9 3-CH₃—C₆H₄ A.103-CH₃—C₆H₄ A.11 2,4-Cl₂—C₆H₃ A.12 2,5-Cl₂—C₆H₃ A.13 2-F—4-Cl—C₆H₃ A.142-F—5-Cl—C₆H₃ A.15 2-Cl—4-CH₃—C₆H₃ A.16 2-CH₃—4-Cl—C₆H₃ A.172-CH₃—5-Cl—C₆H₃ A.18 2-Cl—5-CH₃—C₆H₃ A.19 2,4-(CH₃)₂—C₆H₃ A.202,5-(CH₃)₂—C₆H₃ A.21 3,5-(CH₃)₂—C₆H₃ A.22 2,3,5-(CH₃)₃—C₆H₂ A.232,4,5-(CH₃)₃—C₆H₂ A.24 2-CH₃—4-isopropyl—C₆H₃ A.252-CH₃—4-tert-butyl—C₆H₃ A.26 2-CH₃—4-phenyl—C₆H₃ A.272-CH₃—5-phenyl—C₆H₃ A.28 3-OH—C₆H₄ A.29 2-CH₃—4-OH—C₆H₃ A.302-CH₃—5-OH—C₆H₃ A.31 3-OCH₃—C₆H₄ A.32 4-OCH₃—C₆H₄ A.33 3-OEt—C₆H₄ A.344-OEt—C₆H₄ A.35 2-CH₃—4-OCH₃—C₆H₃ A.36 2-CH₃—4-OC₂H₅—C₆H₃ A.372-CH₃—4-O—n-propyl—C₆H₃ A.38 2-CH₃—4-O—n-butyl—C₆H₃ A.392-CH₃—4-O—phenyl—C₆H₃ A.40 3-O—Phenyl—C₆H₄ A.41 4-O—Phenyl—C₆H₄ A.421-Naphthyl A.43 2-Naphthyl A.44 3-COCH₃—C₆H₄ A.45 4-COCH₃—C₆H₄ A.462-CH₃—4-OCH₃—C₆H₃ A.47 2-CH₃—5-COCH₃—C₆H₃ A.48 2-CH₃—4-CHO—C₆H₃ A.492-CH₃—5-CHO—C₆H₃ A.50 3-CHO—C₆H₄ A.51 2-Cl—4-COCH₃—C₆H₃ A.522,5-(CH₃)₂—4-COCH₃—C₆H₂ A.53 2-CH₃—5-Cl—4-COCH₃—C₆H₂ A.543-[C(CH₃)═NOH]—C₆H₄ A.55 3-[C(CH₃)═NOCH₃]—C₆H₄ A.563-[C(CH₃)═NOCH₂CH₃]—C₆H₄ A.57 3-[C(CH₃)═NOCH₂CH₂CH₃]—C₆H₄ A.583-[C(CH₃)═NOCH₂CH═CH₂]—C₆H₄ A.59 3-[C(CH₃)═NOCH₂C≡CH]—C₆H₄ A.602-CH₃—4-[C(CH₃)═NOCH₃]—C₆H₃ A.61 2-CH₃—4-[C(CH₃)═NOCH₂CH₃]—C₆H₃ A.622-CH₃—4-[C(CH₃)═NOCH₂CH₂CH₃]—C₆H₃ A.63 2-CH₃—4-[C(CH₃)═NOCH₂CH═CH₂]—C₆H₃A.64 2-CH₃—4-[C(CH₃)═NOCH₂—C≡CH]—C₆H₃ A.652,5-(CH₃)₂—4-[C(CH₃)═NOCH₃]—C₆H₂ A.662,5-(CH₃)₂—4-[C(CH₃)═NOCH₂CH₃]—C₆H₂ A.672,5-(CH₃)₂—4-[C(CH₃)═NOCH₂CH₂CH₃]—C₆H₂ A.682,5-(CH₃)₂—4-[C(CH₃)═NOCH₂CH═CH₂]—C₆H₂ A.692,5-(CH₃)₂—4-[C(CH₃)═NOCH₂—C≡CH]—C₆H₂ A.70 2-CH₃—5-[C(CH₃)═NOCH₃]—C₆H₃A.71 2-CH₃—5-[C(CH₃)═NOCH₂CH₃]—C₆H₃ A.722-CH₃—5-[C(CH₃)NOCH₂CH₂CH₃]—C₆H₅ A.73 2-CH₃—5-[C(CH₃)═NOCH₂—CH═CH₂]—C₆H₃A.74 2-CH₃—5-[C(CH₃)═NOCH₂C≡CH]—C₆H₃ A.752-CH₃—5-Cl—4-[C(CH₃)═NOCH₃]—C₆H₂ A.76 2-CH₃—4-[C(CH₂CH₃)═NOCH₃]—C₆H₃A.77 2-CH₃—4-[C(CH₂CH₃)═NOCH₂CH₃]—C₆H₃ A.78 2-Pyridyl A.796-Methyl-2-pyridyl A.80 6-n-Propyl-2-pyridyl A.81 6-n-Butyl-2-pyridylA.82 6-tert-Butyl-2-pyridyl A.83 6-n-Pentyl-2-pyridyl A.846-n-Hexyl-2-pyridyl A.85 6-Phenyl-2-pyridyl A.86 6-Benzyl-2-pyridyl A.876-Trifluoromethyl-2-pyridyl A.88 6-Methoxy-2-pyridyl A.896-Chloro-2-pyridyl A.90 3,6-Dimethyl-2-pyridyl A.913,6-Diethyl-2-pyridyl A.92 4,6-Dimethyl-2-pyridyl A.935,6-Dimethyl-2-pyridyl A.94 4-Phenyl-6-methyl-2-pyridyl A.954,6-Diphenyl-2-pyridyl A.96 3,4-Dichloro-6-methyl-2-pyridyl A.973,4,5-Trichloro-6-phenyl-2-pyridyl A.984-Trifluoromethyl-6-methyl-2-pyridyl A.993-Acetyl-4,6-dimethyl-2-pyridyl A.100 3-Cyano-6-methyl-2-pyridyl A.1013-Cyano-6-ethyl-2-pyridyl A.102 3-Cyano-6-n-propyl-2-pyridyl A.1033-Cyano-6-isopropyl-2-pyridyl A.104 3-Cyano-6-cyclopropyl-2-pyridylA.105 3-Cyano-6-n-butyl-2-pyridyl A.106 3-Cyano-6-tert-butyl-2-pyridylA.107 3-Cyano-6-cyclohexyl-2-pyridyl A.108 3-Cyano-6-phenyl-2-pyridylA.109 3-Methoxycarbonyl-6-isopropyl-2-pyridyl A.1103-Ethyloxycarbonyl-6-isopropyl-2-pyridyl A.1113-Cyano-4,6-dimethyl-2-pyridyl A.112 3,5,6-Trichloro-2-pyridyl A.1135-Trifluoromethyl-2-pyridyl A.114 3-Chloro-5-trifluoromethyl-2-pyridylA.115 6-Cyclopropyl-2-pyridyl A.116 6-Bromo-2-pyridyl A.1174-Trifluoromethyl-2-pyridyl A.118 4-Trifluoromethyl-5-chloro-2-pyridylA.119 4-tert-Butyl-2-pyridyl A.120 3,6-Bis(trifluoromethyl)-2-pyridylA.121 5-Trifluoromethyl-2-pyridyl A.122 3-Fluoro-2-pyridyl A.1233-Chloro-2-pyridyl A.124 4-Bromo-2-pyridyl A.125 5-Methyl-2-pyridylA.126 3-Fluoro-5-trifluoromethyl-2-pyridyl A.1273,6-Dichloro-5-trifluoromethyl-2-pyridyl A.1286-Chloro-4-cyano-2-pyridyl A.129 3-Cyano-5-nitro-2-pyridyl A.1304,6-Difluoro-2-pyridyl A.131 3,5-Dichloro-6-fluoro-2-pyridyl A.1326-Methoxy-3-nitro-2-pyridyl A.133 4-Cyano-6-fluoro-2-pyridyl A.1344-Cyano-3,5,6,-trifluoro-2-pyridyl A.135 6-Chloro-5-nitro-2-pyridylA.136 4,6-Dicyano-2-pyridyl A.137 5-Trichloromethyl-2-pyridyl A.1385-Cyano-2-pyridyl A.139 5-Bromo-4-trifluoromethyl-2-pyridyl A.1403-Nitro-5-trifluoromethyl-2-pyridyl A.141 5-Formamido-2-pyridyl A.1425-Amino-2-pyridyl A.143 5-Nitro-2-pyridyl A.1444-Methyl-5-nitro-2-pyridyl A.145 5-Difluoromethyl-2-pyridyl A.1465-Fluoromethyl-2-pyridyl A.147 5-Methoxycarbonyl-2-pyridyl A.1485-Chloro-6-methoxy-2-pyridyl A.149 5,6-Dichloro-2-pyridyl A.1506-Bromo-5-chloro-2-pyridyl A.151 5-Chloro-6-acetoxy-2-pyridyl A.1525-Bromo-6-fluoro-2-pyridyl A.153 5-Bromo-6-cyano-2-pyridyl A.1545-Bromo-6-hydroxy-2-pyridyl A.155 5-Bromo-6-methoxy-2-pyridyl A.1565,6-Dibromo-2-pyridyl A.157 6-Phenoxy-2-pyridyl A.158 4-Phenyl-2-pyridylA.159 4-Phenoxy-2-pyridyl A.160 6-Hydroxy-2-pyridyl A.1616-Ethoxy-2-pyridyl A.162 6-Benzyloxy-2-pyridyl A.1634-Benzyloxy-2-pyridyl A.164 4,6-Bis(trifluoromethyl)-2-pyridyl A.1656-Formyl-2-pyridyl A.166 6-Amino-2-pyridyl A.167 4-Amino-2-pyridyl A.1684-Carboxy-2-pyridyl A.169 3-Bromo-5-trifluoromethyl-2-pyridyl A.1706-Methyl-3-nitro-2-pyridyl A.171 3-Nitro-2-pyridyl A.1723-Fluoro-5-trifluoromethyl-2-pyridyl A.173 3-Pyridyl A.1742-Fluoro-3-pyridyl A.175 4-Trifluoromethyl-3-pyridyl A.1765-Methyl-3-pyridyl A.177 6-Methoxy-3-pyridyl A.1784-Cyano-2,5,6,-trifluoro-3-pyridyl A.179 4-Pyridyl A.1802-Chloro-4-pyridyl A.181 3-Trifluoromethyl-4-pyridyl A.1822-Chloro-6-fluoro-4-pyridyl A.183 2,3,5,6-Tetrafluoro-4-pyridyl A.1842-Pyrimidinyl A.185 4,6-Dimethyl-2-pyrimidinyl A.1864-Trifluoromethyl-2-pyrimidinyl A.187 4,5,6-Trimethyl-2-pyrimidinylA.188 4-Benzyl-6-methyl-2-pyrimidinyl A.1894-Methyl-6-phenyl-2-pyrimidinyl A.190 4,6-Dimethyl-5-chloro-pyrimidinylA.191 4-Fluoro-2-pyrimidinyl A.192 5-Methyl-2-pyrimidinyl A.1934,6-Difluoro-2-pyrimidinyl A.194 4-Methyl-2-pyrimidinyl A.1954-Pyrimidinyl A.196 2,6-Dimethyl-4-pyrimidinyl A.1972,6-Bis(trifluoromethyl)-4-pyrimidinyl A.1982-Chloromethyl-6-methyl-4-pyrimidinyl A.1992-Methyl-6-chloromethyl-4-pyrimidinyl A.2002-iso-Propyl-6-methyl-4-pyrimidinyl A.2012-iso-Propyl-6-chloromethyl-4-pyrimidinyl A.2022-cyclo-Propyl-6-chloromethyl-4-pyrimidinyl A.2032-cyclo-Propyl-6-methyl-4-pyrimidinyl A.2042-Methyl-6-methoxymethyl-4-pyrimidinyl A.2052-iso-Propyl-6-methoxymethyl-4-pyrimidinyl A.206 2-Phenyl-4-pyrimidinylA.207 2,5-Dimethyl-4-pyrimidinyl A.2082-Methylthio-6-trifluoromethyl-4-pyrimidinyl A.2092-Methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl A.2102-Methylthio-5-n-octyl-6-methyl-4-pyrimidinyl A.2112-Methyl-6-trifluoromethyl-4-pyrimidinyl A.2122-n-Propyl-6-trifluoromethyl-4-pyrimidinyl A.2132-iso-Propyl-6-trifluoromethyl-4-pyrimidinyl A.2142-n-Propyl-6-methyl-4-pyrimidinyl A.2152-tert-Butyl-6-trifluoromethyl-4-pyrimidinyl A.2162-Methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl A.2172-n-Propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl A.2182-iso-Propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl A.2192-tert-Butyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl A.2202-Chloro-4-pyrimidinyl A.221 5-Methoxy-4-pyrimidinyl A.2226-Trifluoromethyl-4-pyrimidinyl A.2232-Chloro-6-trichloromethyl-4-pyrimidinyl A.2242,6-Dichloro-4-pyrimidinyl A.2252-Phenyl-6-trifluoromethyl-4-pyrimidinyl A.2262-Methylthio-6-difluoromethoxy-4-pyrimidyl A.2272-Ethyl-6-trifluoromethyl-4-pyrimidinyl A.2282-Cyclo-propyl-6-trifluoromethyl-4-pyrimidinyl A.2292-Phenyl-6-trifluoromethyl-4-pyrimidinyl A.2302-Methylthio-5-chloro-6-methoxy-4-pyrimidinyl A.2312-Dimethylamino-5-n-butyl-6-methyl-4-pyrimidinyl A.2322-Dimethylamino-5-nitro-6-methyl-4-pyrimidinyl A.233 2-Quinolyl A.2343-Methyl-2-quinolyl A.235 4-Methyl-2-quinolyl A.236 4-Ethyl-2-quinolylA.237 4-Phenyl-2-quinolyl A.238 6-Methyl-2-quinolyl A.2396-Chloro-2-quinolyl A.240 8-Methyl-2-quinolyl A.241 8-Chloro-2-quinolylA.242 4-Ethoxycarbonyl-2-quinolyl A.243 3,4-Dimethyl-2-quinolyl A.2444-Methyl-8-methoxy-2-quinolyl A.245 4-Phenyl-8-ethoxy-2-quinolyl A.2464-Methyl-8-chloro-2-quinolyl A.247 4-Methyl-8-fluoro-2-quinolyl A.2484-Quinolyl A.249 2-Methyl-4-quinolyl A.250 2-Trichloromethyl-4-quinolylA.251 2-Trifluoromethyl-2-quinolyl A.252 2-iso-Propyl-4-quinolyl A.2532-n-Pentyl-4-quinolyl A.254 2-Phenyl-4-quinolyl A.2552-Methoxycarbonyl-4-quinolyl A.256 2,6-Dimethyl-4-quinolyl A.2572-Methyl-6-chloro-4-quinolyl A.258 8-Quinolyl A.259 2-Methyl-8-quinolylA.260 5,7-Dichloro-8-quinolyl A.261 2-Pyrazinyl A.2626-Chloro-2-pyrazinyl A.263 5-Methyl-2-pyrazinyl A.264 3-PyridazinylA.265 5-Chloro-3-pyridazinyl A.266 2-Thienyl A.267 3-Thienyl A.2684-Chloro-3-thienyl A.269 2-Chloro-3-thienyl A.270 5-Chloro-3-thienylA.271 4-Chloro-2-thienyl A.272 5-Chloro-2-thienyl A.273 2-QuinoxalinylA.274 3-Methyl-2-quinoxalinyl A.275 7,8-Dimethyl-2-quinoxalinyl A.2767,8-Dichloro-2-quinoxalinyl A.277 7-Methyl-2-quinoxalinyl A.2788-Methyl-2-quinoxalinyl A.279 7-Methoxy-2-quinoxalinyl A.2803-Phenyl-5-isoxazolyl A.281 2-Benzoxazolyl A.282 2-Benzothiazolyl A.2831-Phenyl-pyrazol-4-yl A.284 2-n-Propyl-6-methyl-4-pyrimidinyl A.2852-n-Propyl-6-methyl-4-pyrimidinyl A.2862-Cyclopentyl-6-trifluoromethyl-4-pyrimidyl A.2872-Cyclohexyl-6-trifluoromethyl-4-pyrimidyl A.2882-Cyclohexyl-5-chloro-6-methyl-4-pyrimidyl A.2892-n-Propyl-5-chloro-6-methyl-4-pyrimidyl A.290 Pyrazol-1-yl A.2914-Chloropyrazol-1-yl

TABLE B B.1 C₆H₅ B.2 2-F—C₆H₄ B.3 3-F—C₆H₄ B.4 4-F—C₆H₄ B.5 2-Cl—C₆H₄B.6 3-Cl—C₆H₄ B.7 4-Cl—C₆H₄ B.8 2-CH₃—C₆H₄ B.9 3-CH₃—C₆H₄ B.103-CH₃—C₆H₄ B.11 2,4-Cl₂—C₆H₃ B.12 2,5-Cl₂—C₆H₃ B.13 2-F—4-Cl—C₆H₃ B.142-F—5-Cl—C₆H₃ B.15 2-Cl—4-CH₃—C₆H₃ B.16 2-CH₃—4-Cl—C₆H₃ B.172-CH₃—5-Cl—C₆H₃ B.18 2-Cl—5-CH₃—C₆H₃ B.19 2-4-(CH₃)₂—C₆H₃ B.202-5-(CH₃)₂—C₆H₃ B.21 3,5-(CH₃)₂—C₆H₃ B.22 2,3,5-(CH₃)₃—C₆H₂ B.232,4,5-(CH₃)₃—C₆H₂ B.24 2-CH₃—4-isopropyl—C₆H₃ B.252-CH₃—4-tert-butyl—C₆H₃ B.26 2-CH₃—4-phenyl—C₆H₃ B.272-CH₃—5-phenyl—C₆H₃ B.28 3-OH—C₆H₄ B.29 2-CH₃—4-OH—C₆H₃ B.302-CH₃—5-OH—C₆H₃ B.31 3-OCH₃—C₆H₄ B.32 4-OCH₃—C₆H₄ B.33 3-OEt—C₆H₄ B.344-OEt—C₆H₄ B.35 2-CH₃—4-OCH₃—C₆H₃ B.36 2-CH₃—4-OC₂H₅—C₆H₃ B.372-CH₃—4-O—n-propyl—C₆H₃ B.38 2-CH₃—4-O—n-butyl—C₆H₃ B.392-CH₃—4-O—phenyl—C₆H₃ B.40 3-O—phenyl—C₆H₄ B.41 4-O—phenyl—C₆H₄ B.421-Naphthyl B.43 2-Naphthyl B.44 3-COCH₃—C₆H₄ B.45 4-COCH₃—C₆H₄ B.462-CH₃-4-OCH₃—C₆H₃ B.47 2-CH₃-5-COCH₃—C₆H₃ B.48 2-CH₃-4-CHO—C₆H₃ B.492-CH₃-5-CHO—C₆H₃ B.50 3-CHO—C₆H₄ B.51 2-Cl—4-COCH₃—C₆H₃ B.522,5-(CH₃)₂-4-COCH₃—C₆H₂ B.53 2-CH₃-5-Cl—4-COCH₃—C₆H₂ B.543-(2-F—OC₆H₄)—C₆H₄ B.55 3-(2-CH₃—OC₆H₄)—C₆H₄ B.56 3-(2-Cl—OC₆H₄)—C₆H₄B.57 3-(2-CN—OC₆H₄)—C₆H₄ B.58 3-(2-CO₂CH₃—OC₆H₄)—C₆H₄ B.593-(2,4-F₂—OC₆H₃)—C₆H₄ B.60 3-(2,6-F₂—OC₆H₃)—C₆H₄ B.613-(2,5-F₂—OC₆H₃)—C₆H₄ B.62 3-(2,6-Cl₂—OC₆H₃)—C₆H₄ B.633-(2,4-Cl—OC₆H₃)—C₆H₄ B.64 3-[2,4-(CH₃)₂—OC₆H₃)—C₆H₄ B.653-[2,6-(CH₃)₂—OC₆H₃)—C₆H₄ B.66 3-(3-F—OC₆H₄)—C₆H₄ B.673-(3-Cl—OC₆H₄)—C₆H₄ B.68 3-(3-CH₃—OC₆H₄)—C₆H₄ B.69 3-(4-F—OC₆H₄)—C₆H₄B.70 3-(4-Cl—OC₆H₄)—C₆H₄ B.71 3-(4-CH₃—OC₆H₄)—C₆H₄ B.723-(3-iso-Propyl—OC₆H₄)—C₆H₄ B.73 3-(3-tert-Butyl—OC₆H₄)—C₆H₄ B.743-(4-Isopropyl—OC₆H₄)—C₆H₄ B.75 3-(4-tert-Butyl—OC₆H₄)—C₆H₄ B.763-Fluoropyridin-2-yl B.77 3-Chloropyridin-2-yl B.78 3-Bromopyridin-2-ylB.79 3-Methylpyridin-2-yl B.80 3-Trifluoromethylpyridin-2-yl B.813-Methoxypyridin-2-yl B.82 4-Fluoropyridin-2-yl B.834-Chloropyridin-2-yl B.84 4-Bromopyridin-2-yl B.85 4-Methylpyridin-2-ylB.86 4-Trifluoromethylpyridin-2-yl B.87 4-Methoxypyridin-2-yl B.885-Fluoropyridin-2-yl B.89 5-Chloropyridin-2-yl B.90 5-Bromopyridin-2-ylB.91 5-Methylpyridin-2-yl B.92 5-Methoxypyridin-2-yl B.936-Fluoropyridin-2-yl B.94 6-Chloropyridin-2-yl B.95 6-Bromopyridin-2-ylB.96 6-Methylpyridin-2-yl B.97 6-Trifluoromethylpyridin-2-yl B.986-Methoxypyridin-2-yl B.99 2-Fluoropyridin-3-yl B.1002-Chloropyridin-3-yl B.101 2-Bromopyridin-3-yl B.1022-Methylpyridin-3-yl B.103 2-Trifluoromethylpyridin-3-yl B.1043-Methoxypyridin-3-yl B.105 4-Fluoropyridin-3-yl B.1064-Chloropyridin-3-yl B.107 4-Bromopyridin-3-yl B.1084-Methylpyridin-3-yl B.109 4-Trifluoromethylpyridin-3-yl B.1104-Methoxypyridin-3-yl B.111 5-Fluoropyridin-3-yl B.1125-Chloropyridin-3-yl B.113 5-Bromopyridin-3-yl B.1145-Methylpyridin-3-yl B.115 5-Trifluoromethylpyridin-3-yl B.1165-Methoxypyridin-3-yl B.117 6-Fluoropyridin-3-yl B.118 Pyridin-2-ylB.119 Pyridin-3-yl B.120 Pyridin-4-yl B.121 6-Chloropyridin-3-yl B.1226-Bromopyridin-3-yl B.123 6-Methylpyridin-3-yl B.1246-Trifluoromethylpyridin-3-yl B.125 6-Methoxypyridin-3-yl B.1262-Fluoropyridin-4-yl B.127 2-Chloropyridin-4-yl B.1282-Bromopyridin-4-yl B.129 2-Methylpyridin-4-yl B.1302-Trifluoromethylpyridin-4-yl B.131 2-Methoxypyridin-4-yl B.1323-Fluoropyridin-4-yl B.133 3-Chloropyridin-4-yl B.1343-Bromopyridin-4-yl B.135 3-Methylpyridin-4-yl B.1363-Trifluoromethylpyridin-4-yl B.137 3-Methoxypyridin-4-yl B.1384-Fluoropyrimidin-2-yl B.139 4-Chloropyrimidin-2-yl B.1404-Bromopyrimidin-2-yl B.141 4-Methylpyrimidin-2-yl B.1424-Trifluoromethylpyrimidin-2-yl B.143 4-Methoxypyrimidin-2-yl B.1445-Fluoropyrimidin-2-yl B.145 5-Chloropyrimidin-2-yl B.1465-Bromopyrimidin-2-yl B.147 5-Methylpyrimidin-2-yl B.1485-Trifluoromethylpyrimidin-2-yl B.149 5-Methoxypyrimidin-2-yl B.1502-Fluoropyrimidin-4-yl B.151 2-Chloropyrimidin-4-yl B.1522-Bromopyrimidin-4-yl B.153 2-Methylpyrimidin-4-yl B.1542-Trifluoromethylpyrimidin-4-yl B.155 2-Methoxypyrimidin-4-yl B.1565-Fluoropyrimidin-4-yl B.157 5-Chloropyrimidin-4-yl B.1585-Bromopyrimidin-4-yl B.159 5-Methoxypyrimidin-4-yl B.1605-Trifluoromethylpyrimidin-4-yl B.161 5-Methoxypyrimidin-4-yl B.1626-Fluoropyrimidin-4-yl B.163 6-Chloropyrimidin-4-yl B.1646-Bromopyrimidin-4-yl B.165 6-Methylpyrimidin-4-yl B.1666-Trifluoromethylpyrimidin-4-yl B.167 6-Methoxypyrimidin-4-yl B.1682-Fluoropyrimidin-5-yl B.169 2-Chloropyrimidin-5-yl B.1702-Bromopyrimidin-5-yl B.171 2-Methylpyrimidin-5-yl B.1722-Trifluoromethylpyrimidin-5-yl B.173 2-Methoxypyrimidin-5-yl B.1744-Fluoropyrimidin-5-yl B.175 4-Chloropyrimidin-5-yl B.1764-Bromopyrimidin-5-yl B.177 4-Methylpyrimidin-5-yl B.1784-Trifluoromethylpyrimidin-5-yl B.1793-Fluoro-5-trifluoromethylpyridin-2-yl B.1803,6-Dichloro-5-trifluoromethylpyridin-2-yl B.1815,6-Dichloro-3-trifluoromethylpyridin-2-yl B.1825-Chloro-3-trifluoromethylpyridin-2-yl B.1833-Chloro-5-trifluoromethylpyridin-2-yl B.1846-Chloro-4-cyanopyridin-2-yl B.185 3-Cyano-5-nitropyridin-2-yl B.1862-Chloro-6-fluoropyridin-4-yl B.187 6-Chloro-4-fluoropyridin-2-yl B.1884,6-Difluoropyridin-2-yl B.189 3,5-Dichloro-6-fluoropyridin-2-yl B.1906-Methoxy-3-nitropyridin-2-yl B.191 4-Cyano-6-fluoropyridin-2-yl B.1926-Chloro-5-cyanopyridin-2-yl B.193 6-Chloro-3-cyanopyridin-2-yl B.1944-Cyano-3,5,6-trifluoropyridin-2-yl B.195 6-Chloro-5-nitropyridin-2-ylB.196 6-Chloro-3-nitropyridin-2-yl B.197 5-Cyano-6-fluoropyridin-2-ylB.198 3-Cyano-6-fluoropyridin-2-yl B.199 4,6-Dicyanopyridin-2-yl B.2005-Trichloromethylpyridin-2-yl B.201 5-Cyanopyridin-2-yl B.2025-Bromo-4-trifluoromethylpyridin-2-yl B.2033-Nitro-5-trifluoromethylpyridin-2-yl B.204 5-Formamidopyridin-2-ylB.205 5-Aminopyridin-2-yl B.206 2,3,5,6-Tetrafluoropyridin-4-yl B.2075-Nitropyridin-2-yl B.208 4-Methyl-5-nitropyridin-2-yl B.2095-Difluoromethylpyridin-2-yl B.210 5-Fluoromethylpyridin-2-yl B.2114,6-Difluoropyrimidin-2-yl B.212 2,6-Difluoropyrimidin-4-yl B.2132-Chloro-6-trichloromethylpyrimidin-4-yl B.2142,6-Dichloropyrimidin-4-yl B.215 5-Methoxycarbonylpyridin-2-yl B.2165-Chloro-6-fluoropyridin-2-yl B.217 5-Chloro-6-hydroxypyridin-2-yl B.2185-Chloro-6-methoxypyridin-2-yl B.219 5-Chloro-6-cyanopyridin-2-yl B.2205,6-Dichloropyridin-2-yl B.221 6-Bromo-5-chloropyridin-2-yl B.2225-Chloro-6-acetoxypyridin-2-yl B.223 5-Bromo-6-fluoropyridin-2-yl B.2245-Bromo-6-chloropyridin-2-yl B.225 5-Bromo-6-cyanopyridin-2-yl B.2265-Bromo-6-hydroxypyridin-2-yl B.227 5-Bromo-6-methoxypyridin-2-yl B.2285,6-Dibromopyridin-2-yl B.229 4-Cyanopyridin-2-yl B.2306-Cyanopyridin-2-yl B.231 5-Chloropyridin-2-yl B.2325-Chloropyridin-2-yl B.233 4-Chloro-6-methylpyrimidin-2-yl B.2342-Chloro-6-fluoropyridin-4-yl B.2355-Bromo-4-trifluoromethylpyridin-2-yl B.236 4,5-Dichloropyridin-2-ylB.237 4,5-Dibromopyridin-2-yl B.238 5,6-Dichloropyridin-2-yl B.2394,6-Dichloropyridin-2-yl B.240 4,6-Dibromopyridin-2-yl B.2415,6-Dibromopyridin-2-yl B.242 4-Bromo-5-chloropyridin-2-yl B.2436-Bromo-5-chloropyridin-2-yl B.244 5-Bromo-4-chloropyridin-2-yl B.2455-Bromo-4-chloropyridin-21y1 B.246 6-Bromo-4-chloropyridin-2-yl B.2474-Bromo-6-chloropyridin-2-yl B.248 6-Chloro-4-methoxypyridin-2-yl B.2496-Bromo-4-methoxypyridin-2-yl B.250 6-Chloroquinazolin-2-yl B.251Quinazolin-2-yl B.252 5-Benzyloxycarbonylpyridin-2-yl B.2534-Formylpyridin-2-yl B.254 5-Formylpyridin-2-yl B.2556-Formylpyridin-2-yl B.256 4-Cyanopyridin-2-yl B.257 6-Cyanopyridin-2-ylB.258 5-Hydroxymethylpyridin-2-yl B.2596-Chloro-4-trifluoromethylpyridin-2-yl B.2606-Chloro-4-trifluoromethylpyridin-2-yl B.2616-Chloro-4-methylpyridin-2-yl B.262 2,5-Dichloro-6-cyanopyridin-2-ylB.263 2,5-Dichloro-6-carboxypyridin-2-yl B.2642,5-Dichloro-6-methoxycarbonyl-pyridin-2-yl B.265 4-Cyanopyridin-2-ylB.266 6-Trifluoromethylpyridin-2-yl B.267 6-Methoxycarbonylpyridin-2-ylB.268 6-Carboxypyridin-2-yl B.269 4-Phenoxypyridin-2-yl B.2705-Phenoxypyridin-2-yl B.271 6-Phenoxypyridin-2-yl B.2726-Chloropyridin-3-yl B.273 1-Phenoxypyrimidin-4-yl B.2741-(4-Methylphenoxy)pyrimidin-4-yl B.275 4-Phenoxypyrimidin-2-yl B.2764-(2-Fluorophenoxy)pyrimidin-2-yl B.277 4-Phenoxypyrimidin-6-yl B.2784-(4-Chlorophenoxy)pyrimidin-6-yl B.279 4-(2-Pyridyloxy)pyrimidin-6-ylB.280 4-(6-Chloro-2-pyridyloxy)pyrimidin-6-yl B.2814-(3-Pyridyloxy)pyrimidin-6-yl B.2824-(2-Methyl-3-pyridyloxy)pyrimidin-6-yl B.2834-(4-Pyridyloxy)pyrimidin-6-yl B.284 2-Furanyl B.285 3-Furanyl B.2864-Chloro-2-thienyl B.287 5-Chloro-2-thienyl B.288 5-Bromo-2-thienylB.289 5-Nitro-2-thienyl B.290 3-Thienyl B.291 2-Chloro-3-thienyl B.2922-Bromo-3-thienyl B.293 1-Methyl-3-pyrrolyl B.294 1-Methyl-2-pyrroiylB.295 1-Benzofuran-2-yl B.296 1-Benzofuran-3-yl B.2971-Benzothiophen-2-yl B.298 1-Benzothiophen-3-yl B.299 3-Pyrrolyl B.3002-Pyrrolyl B.301 3-Indolyl B.302 2-Indolyl B.303 1-Methyl-3-indolylB.304 1-Methyl-2-indolyl B.305 1-Methylpyrazol-4-yl B.3061-Methylpyrazol-3-yl B.307 1-Methylpyrazol-5-yl B.308 Isoxazol-3-ylB.309 Isoxazol-4-yl B.310 Isoxazol-5-yl B.311 Isothiazol-3-yl B.312Isothiazol-4-yl B.313 Isothiazol-5-yl B.314 Oxazol-2-yl B.315Oxazol-5-yl B.316 Oxazol-4-yl B.317 Thiazol-4-yl B.318 Thiazol-5-ylB.319 Thiazol-2-yl B.320 1-Methylimidazol-4-yl B.3211-Methylimidazol-5-yl B.322 1-Methylimidazol-2-yl B.3231,2-Benzisoxazol-3-yl B.324 1,2-Benzisothiazol-3-yl B.3251-Methylindazol-3-yl B.326 Benzoxazol-2-yl B.327 5-Chlorobenzoxazol-2-ylB.328 6-Fluorobenzoxazol-2-yl B.329 Benzthiazol-2-yl B.3305-Fluorobenzothiazol-2-yl B.331 6-Fluorobenzothiazol-2-yl B.332Pyrido[3,2-d]thiazol-2-yl B.333 (6-Chloropyrido)[3,2-d]thiazol-2-ylB.334 1-Methyl-1,2,3-triazol-5-yl B.335 1-Methyl-1,2,3-triazol-4-ylB.336 1-Methyl-1,3,4-triazol-5-yl B.337 1-Methyl-1,3,4-triazol-3-ylB.338 1-Methyl-1,2,3,4-tetrazol-5-yl B.3392-Methyl-1,2,3,4-tetrazol-5-yl B.3405-Trifluoromethyl-1,3,4-thiadiazol-2-yl B.341 6-Chlorobenzoxazol-2-ylB.342 5-Fluorobenzoxazol-2-yl B.343 5-Nitrothiazol-2-yl

TABLE C C.1 Phenyl C.2 2-Fluorophenyl C.3 3-Fluorophenyl C.44-Fluorophenyl C.5 Pentafluorophenyl C.6 Pentafluorophenyl C.7Pentafluorophenyl C.8 Pentafluorophenyl C.9 Pentafluorophenyl C.10Pentafluorophenyl C.11 Pentafluorophenyl C.12 Pentafluorophenyl C.132-Chlorophenyl C.14 3-Chlorophenyl C.15 4-Chlorophenyl C.16Pentachlorophenyl C.17 2,3-Dichlorophenyl C.18 2,4-Dichlorophenyl C.192,5-Dichlorophenyl C.20 2,6-Dichlorophenyl C.21 3,4-Dichlorophenyl C.223,5-Dichlorophenyl C.23 2,3,4-Trichlorophenyl C.24 2,3,5-TrichlorophenylC.25 2,3,6-Trichlorophenyl C.26 2-Cyanophenyl C.27 3-Cyanophenyl C.284-Cyanophenyl C.29 2-Nitrophenyl C.30 3-Nitrophenyl C.31 4-NitrophenylC.32 2-Methylphenyl C.33 3-Methylphenyl C.34 4-Methylphenyl C.352,4-Dimethylphenyl C.36 2,6-Dimethylphenyl C.37 3,4-Dimethylphenyl C.383,5-Dimethylphenyl C.39 2,3,4-Trimethylphenyl C.40 2,3,5-TrimethylphenylC.41 2,3,6-Trimethylphenyl C.42 2,4,5-Trimethylphenyl C.432,4,6-Trimethylphenyl C.44 3,4,5-Trimethylphenyl C.45 PentamethylphenylC.46 2-Ethylphenyl C.47 3-Ethylphenyl C.48 4-Ethylphenyl C.493,5-Diethylphenyl C.50 2-n-Propylphenyl C.51 3-n-Propylphenyl C.524-n-Propylphenyl C.53 2-Isopropylphenyl C.54 3-Isopropylphenyl C.554-Isopropylphenyl C.56 2,4-Di-iso-Propylphenyl C.573,5-Di-iso-Propylphenyl C.58 4-n-Butylphenyl C.59 4-sec-Butylphenyl C.604-iso-Butylphenyl C.61 4-tert-Butylphenyl C.62 3-tert-Butylphenyl C.632-tert-Butylphenyl C.64 2,4-Di-tert-Butylphenyl C.652,5-Di-tert-Butylphenyl C.66 4-n-Hexylphenyl C.67 4-n-Dodecylphenyl C.682-Methyl-4-tert-butylphenyl C.69 2-Methyl-6-tert-butylphenyl C.702-Methyl-4-iso-propylphenyl C.71 2-Methyl-4-cyclohexylphenyl C.722-Methyl-4-phenylphenyl C.73 2-Methyl-4-benzylphenyl C.742-Methyl-5-phenoxyphenyl C.75 2-Methyl-4-benzyloxyphenyl C.762-Methyl-3-chlorophenyl C.77 2-Methyl-4-chlorophenyl C.782-Methyl-5-chlorophenyl C.79 2-Methyl-6-chlorophenyl C.802-Methyl-4-fluorophenyl C.81 2-Methyl-3-bromophenyl C.822-Methyl-4-bromophenyl C.83 2-Methyl-3-methoxyphenyl C.842-Methyl-4-methoxyphenyl C.85 2-Methyl-5-methoxyphenyl C.862-Methyl-6-methoxyphenyl C.87 2-Methyl-4-isopropoxyphenyl C.882-Methyl-2,5-dimethoxyphenyl C.89 2-Methoxyphenyl C.90 3-MethoxyphenylC.91 4-Methoxyphenyl C.92 2,3-Dimethoxyphenyl C.93 2,4-DimethoxyphenylC.94 2,5-Dimethoxyphenyl C.95 2,6-Dimethoxyphenyl C.963,4-Dimethoxyphenyl C.97 3,5-Dimethoxyphenyl C.98 3,6-DimethoxyphenylC.99 2,3,4-Trimethoxyphenyl C.100 2,3,5-Trimethoxyphenyl C.1012,3,6-Trimethoxyphenyl C.102 2,4,5-Trimethoxyphenyl C.1032,4,6-Trimethoxyphenyl C.104 3,4,5-Trimethoxyphenyl C.105 2-EthoxyphenylC.106 3-Ethoxyphenyl C.107 4-Ethoxyphenyl C.108 2-Isopropoxyphenyl C.1093-Isopropoxyphenyl C.110 4-Isopropoxyphenyl C.111 3-tert-ButoxyphenylC.112 4-tert-Butoxyphenyl C.113 2-Trifluoromethoxyphenyl C.1143-Trifluoromethoxyphenyl C.115 4-Trifluoromethoxyphenyl C.1163-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl C.1174-(1′,1′,2′,2′-Tetrafluoro)ethoxyphenyl C.118 2-Chloromethylphenyl C.1193-Chloromethylphenyl C.120 4-Chloromethylphenyl C.1212-Trifluoromethylphenyl C.122 3-Trifluoromethylphenyl C.1234-Trifluoromethylphenyl C.124 2-(Methoxyiminomethyl)phenyl C.1253-(Methoxyiminomethyl)phenyl C.126 4-(Methoxyiminomethyl)phenyl C.1272-(Ethoxyiminomethyl)phenyl C.128 3-(Ethoxyiminomethyl)phenyl C.1294-(Ethoxyiminomethyl)phenyl C.130 2-(n-Propoxyiminomethyl)phenyl C.1313-(n-Propoxyiminomethyl)phenyl C.132 4-(n-Propoxyiminomethyl)phenylC.133 2-(iso-Propoxyiminomethyl)phenyl C.1343-(iso-Propoxyiminomethyl)phenyl C.135 4-(iso-Propoxyiminomethyl)phenylC.136 2-(n-Butoxyiminomethyl)phenyl C.137 3-(n-Butoxyiminomethyl)phenylC.138 4-(n-Butoxyiminomethyl)phenyl C.1392-(iso-Butoxyiminomethyl)phenyl C.140 3-(iso-Butoxyiminomethyl)phenylC.141 4-(iso-Butoxyiminomethyl)phenyl C.1422-(tert-Butoxyiminomethyl)phenyl C.143 3-(tert-Butoxyiminomethyl)phenylC.144 4-(tert-Butoxyiminomethyl)phenyl C.1452-(n-Pentoxyiminomethyl)phenyl C.146 3-(n-Pentoxyiminomethyl)phenylC.147 4-(n-Pentoxyiminomethyl)phenyl C.148 2-(n-Hexoxyiminomethyl)phenylC.149 3-(n-Hexoxyiminomethyl)phenyl C.150 4-(n-Hexoxyiminomethyl)phenylC.151 2-(Allyloxyimonomethyl)phenyl C.152 3-(Allyloxyimonomethyl)phenylC.153 4-(Allyloxyimonomethyl)phenyl C.154 2-(Benzyloxyiminomethyl)phenylC.155 3-(Benzyloxyiminomethyl)phenyl C.1564-(Benzyloxyiminomethyl)phenyl C.157 2-(Methoxyimino-1′-ethyl)phenylC.158 3-(Methoxyimino-1′-ethyl)phenyl C.1594-(Methoxyimino-1′-ethyl)phenyl C.160 2-(Ethoxyimino-1′-ethyl)phenylC.161 3-(Ethoxyimino-1′-ethyl)phenyl C.1624-(Ethoxyimino-1′-ethyl)phenyl C.163 2-(n-Propoxyimino-1′-ethyl)phenylC.164 3-(n-Propoxyimino-1′-ethyl)phenyl C.1654-(n-Propoxyimino-1′-ethyl)phenyl C.166 2-(n-Butoxyamino-1′-ethyl)phenylC.167 3-(n-Butoxyamino-1′-ethyl)phenyl C.1684-(n-Butoxyamino-1′-ethyl)phenyl C.169 2-(n-Butoxyamino-1′-ethyl)phenylC.170 3-(n-Butoxyamino-1′-ethyl)phenyl C.1714-(n-Butoxyamino-1′-ethyl)phenyl C.172 2-(n-Pentoxyimino-1′-ethyl)phenylC.173 3-(n-Pentoxyimino-1′-ethyl)phenyl C.1744-(n-Pentoxyimino-1′-ethyl)phenyl C.1752-(n-Pentoxyimino-1′-ethyl)phenyl C.1763-(n-Pentoxyimino-1′-ethyl)phenyl C.1774-(n-Pentoxyimino-1′-ethyl)phenyl C.178 2-(n-Hexoxyimino-1′-ethyl)phenylC.179 3-(n-Hexoxyimino-1′-ethyl)phenyl C.1804-(n-Hexoxyimino-1′-ethyl)phenyl C.181 2-(Allyloxyimino-1′-ethyl)phenylC.182 3-(Allyloxyimino-1′-ethyl)phenyl C.1834-(Allyloxyimino-1′-ethyl)phenyl C.184 2-(Benzyloxyimino-1′-ethyl)phenylC.185 3-(Benzyloxyimino-1′-ethyl)phenyl C.1864-(Benzyloxyimino-1′-ethyl)phenyl C.187 2-Phenylphenyl C.1883-Phenylphenyl C.189 4-Phenylphenyl C.190 2-Phenoxyphenyl C.1913-Phenoxyphenyl C.192 4-Phenoxyphenyl C.193 2-Benzyloxyphenyl C.1943-Benzyloxyphenyl C.195 4-Benzyloxyphenyl C.196 4-(Imidazol-1′-yl)phenylC.197 4-(Piperazin-1′-yl)phenyl C.198 4-(Morpholin-1′-yl)phenyl C.1994-(Piperidin-1′-yl)phenyl C.200 4-(Pyridyl-2′-oxy)phenyl C.2012-Cyclopropylphenyl C.202 3-Cyclopropylphenyl C.203 4-CyclopropylphenylC.204 3-Cyclohexylphenyl C.205 4-Cyclohexylphenyl C.206 4-OxiranylphenylC.207 4-(1′,3′-Dioxan-2′-yl)phenyl C.2084-(Tetrahydropyran-2-yloxy)phenyl C.209 1-Naphthyl C.210 2-NaphthylC.211 9-Anthryl C.212 1-Naphthoxy C.213 2-Naphthoxy C.214 9-AnthroxyC.215 Phenoxy C.216 2-Chlorophenoxy C.217 3-Chlorophenoxy C.2184-Chlorophenoxy C.219 4-tert-Butylphenoxy C.220 4-Methoxyphenoxy C.2214-Ethoxyphenoxy C.222 4-tert-Butoxyphenoxy C.223 Phenylthio C.2242-Chlorophenylthio C.225 4-Chlorophenylthio C.226 Benzyl C.2272-Methylbenzyl C.228 3-Methylbenzyl C.229 4-Methylbenzyl C.2304-tert-Butylbenzyl C.231 2-Chlorobenzyl C.232 3-Chlorobenzyl C.2334-Chlorobenzyl C.234 2,4-Dichlorobenzyl C.235 2,6-Dichlorobenzyl C.2362,4,6-Trichlorobenzyl C.237 2-Trifluoromethylbenzyl C.2383-Trifluoromethylbenzyl C.239 4-Trifluoromethylbenzyl C.2402-Methoxybenzyl C.241 4-Methoxybenzyl C.242 4-tert-Butoxybenzyl C.2434-Phenoxybenzyl C.244 1-Phenethyl C.245 2-Phenethyl C.246 1-PhenylpropylC.247 2-Phenylpropyl C.248 3-Phenylpropyl C.249 2-Methyl-2-phenylpropylC.250 2-Methyl-3-phenylpropyl C.251 4-Phenylbutyl C.2522-Phenyl-1-ethenyl C.253 1-Phenyl-1-ethenyl C.254 1-Phenyl-1-propenylC.255 1-Phenyl-1-propen-2-yl C.256 2,2-Diphenylethenyl C.257Phenoxymethyl C.258 3-Pyridyl C.259 3-Pyridyl C.260 4-Pyridyl C.2612,6-Pyrimidinyl C.262 1,5-Pyrimidinyl C.263 2-Thienyl C.264 3-ThienylC.265 2-Furyl C.266 3-Furyl C.267 1-Pyrrolyl C.268 1-Imidazolyl C.2691,3,4-Triazolyl C.270 1,3,4-Triazolyl C.271 4-Thiazolyl C.2722-Benzothiazolyl C.273 2-Pyridyloxy C.274 2-Pyrimidinyloxy C.2752-Pyridylthio C.276 2-Pyrimidinylthio C.277 2-Benzothiazolylthio C.278Phenylthiomethyl C.279 2-Pyridylmethyl C.280 3-Pyridylmethyl C.281Furfuryloxy C.282 Thienylmethoxy C.283 2-Isoxazolylmethoxy C.2842-Oxazolylmethoxy C.285 2-Pyridylmethoxy C.286 2′-Furylethenyl C.2872′-Thienyl-2-ethenyl C.288 3′-Pyridyl-2-ethenyl C.289 Oxiranyl C.2901-Aziridinyl C.291 1-Azetidinyl C.292 1-Pyrrolidinyl C.2932-Tetrahydrofuryl C.294 2-Tetrahydropyranyl C.295 3-TetrahydropyranylC.296 1-Piperidinyl C.297 1-Morpholinyl C.298 1-Piperazinyl C.2991,3-Dioxan-2-yl C.300 3-Tetrahydrothiopyranyl C.301 2-DihydropyranyloxyC.302 2-Tetrahydropyranyloxy C.303 Cyclopropyl C.304 Cyclobutyl C.305Cyclopentyl C.306 Cyclohexyl C.307 1-Methylcyclopropyl C.3082,2-Dimethylcyclopropyl C.309 1-Methylcyclohexyl C.3102,2-Difluorocyclopropyl C.311 2,2-Dichlorocyclopropyl C.3122,2-Dibromocyclopropyl C.313 2,2,-Dichloro-3-Methylcyclopropyl C.3142,2,3,3,-Tetrafluorocyclobutyl C.315 CH₃ C.316 CH₃CH₂ C.317 CH₃CH₂CH₂C.318 CH₂═CH—CH₂ C.319 HC≡C—CH₂ C.320 (CH₃)₃C C.321 Cyclo-C₆H₁₁ C.322C₆H₅—CH₂— C.323 C₆H₅—CH₂O— C.324 (CH₃)₂CH C.325 CH₃O—CH₂

TABLE D No. Y R⁴ D.1 CH₃ H D.2 CH₃ CH₃ D.3 CH₃ C₂H₅ D.4 CH₃ n-C₃H₇ D.5CH₃ i-C₃H₇ D.6 CH₃ Cyclopropyl D.7 CH₃ n-C₄H₉ D.8 CH₃ s-C₄H₉ D.9 CH₃i-C₄H₉ D.10 CH₃ t-C₄H₉ D.11 CH₃ n-C₅H₁₁ D.12 CH₃ i-C₅H₁₁ D.13 CH₃neo-C₅H₁₁ D.14 CH₃ Cyclopentyl D.15 CH₃ n-C₆H₁₃ D.16 CH₃ Cyclohexyl D.17CH₃ n-C₈H₁₇ D.18 CH₃ CH₂CH₂Cl D.19 CH₃ (CH₂)₄Cl D.20 CH₃ CH₂CN D.21 CH₃CH₂CH₂CN D.22 CH₃ (CH₂)₃CN D.23 CH₃ (CH₂)₄CN D.24 CH₃ (CH₂)₆CN D.25 CH₃Cyclopropylmethyl D.26 CH₃ 2-Methoxyeth-1-yl D.27 CH₃ 2-Ethoxyeth-1-ylD.28 CH₃ 2-Isopropoxyeth-1-yl D.29 CH₃ 3-Methoxyprop-1-yl D.30 CH₃3-Ethoxyprop-1-yl D.31 CH₃ 3-Isopropoxyprop-1-yl D.32 CH₃4-Methoxybut-1-yl D.33 CH₃ 4-Isopropoxybut-1-yl D.34 CH₃ Propen-3-ylD.35 CH₃ But-2-en-1-yl D.36 CH₃ 3-Methylbut-2-en-1-yl D.37 CH₃2-Vinyloxyeth-1-yl D.38 CH₃ Allyloxyeth-1-yl D.39 CH₃2-Trifluoromethoxyeth-1-yl D.40 CH₃ 3-Trifluoromethoxyprop-1-yl D.41 CH₃4-Difluoromethoxybut-1-yl D.42 CH₃ 2-Oxopropyl D.43 CH₃ Cyclohexyl D.44CH₃ Cyclopropyl D.45 CH₃ Cyclopentyl D.46 4-F—C₆H₄ H D.47 4-F—C₆H₄ CH₃D.48 4-F—C₆H₄ C₂H₅ D.49 4-F—C₆H₄ n-C₃H₇ D.50 4-F—C₆H₄ i-C₃H₇ D.514-F—C₆H₄ Cyclopropyl D.52 4-F—C₆H₄ n-C₄H₉ D.53 4-F—C₆H₄ t-C₄H₉ D.544-F—C₆H₄ n-C₆H₁₃ D.55 4-F—C₆H₄ (E)-1-Chloropropen-3-yl D.56 CH₂CH₃ HD.57 CH₂CH₃ CH₃ D.58 CH₂CH₃ CH₂CH₃ D.59 CH₂CH₃ n-C₃H₇ D.60 CH₂CH₃CH₂—C≡CH D.61 CH₂CH₃ CH₂—CH═CH₂ D.62 CH₂CH₃ tert-C₄H₉ D.63 C₆H₅ H D.64C₆H₅ CH₃ D.65 C₆H₅ C₂H₅ D.66 C₆H₅ n-C₃H₇ D.67 C₆H₅ i-C₃H₇ D.68 C₆H₅Cyclopropyl D.69 C₆H₅ n-C₄H₉ D.70 C₆H₅ t-C₄H₉ D.71 C₆H₅ n-C₆H₁₃ D.72O—i-C₃H₇ CH₃ D.73 O—i-C₃H₇ CH₂CH₃ D.74 O—CH₂CH₃ CH₃ D.75 O—CH₂CH₃ CH₂CH₃D.76 O—Cyclopropyl CH₃ D.77 H CH₃ D.78 H C₂H₅ D.79 O—CH(CH₂CH₃)₂ CH₃D.80 O—CH(CH₂CH₃)₂ CH₂CH₃ D.81 O—Cyclopentyl CH₃ D.82 OH CH₃ D.83 OHC₂H₅ D.84 OH n-C₃H₇ D.85 OH i-C₃H₇ D.86 Cl CH₃ D.87 Cl C₂H₅ D.88 Cln-C₃H₇ D.89 Cl i-C₃H₇ D.90 OCH₃ H D.91 OCH₃ CH₃ D.92 OCH₃ C₂H₅ D.93 OCH₃n-C₃H₇ D.94 OCH₃ i-C₃H₇ D.95 SCH₃ H D.96 SCH₃ CH₃ D.97 SCH₃ C₂H₅ D.98O—Cyclohexyl CH₃ D.99 O—Cyclohexyl CH₂CH₃ D.100 Cyclopropyl H D.101Cyclopropyl CH₃ D.102 Cyclopropyl C₂H₅ D.103 Cyclopropyl n-C₃H₇ D.104Cyclopropyl i-C₃H₇ D.105 2-Pyridyl H D.106 2-Pyridyl CH₃ D.107 2-PyridylC₂H₅ D.108 2-Pyridyl n-C₃H₇ D.109 2-Pyridyl i-C₃H₇ D.110 3-Pyridyl HD.111 3-Pyridyl CH₃ D.112 3-Pyridyl C₂H₅ D.113 3-Pyridyl n-C₃H₇ D.1143-Pyridyl i-C₃H₇ D.115 4-Pyridyl H D.116 4-Pyridyl CH₃ D.117 4-PyridylC₂H₅ D.118 4-Pyridyl n-C₃H₇ D.119 4-Pyridyl i-C₃H₇ D.120 2-Pyridimidyl HD.121 2-Pyridimidyl CH₃ D.122 2-Pyridimidyl C₂H₅ D.123 2-Pyridimidyln-C₃H₇ D.124 2-Pyridimidyl i-C₃H₇ D.125 4-Pyridimidyl H D.1264-Pyridimidyl CH₃ D.127 4-Pyridimidyl C₂H₅ D.128 4-Pyridimidyl n-C₃H₇D.129 4-Pyridimidyl i-C₃H₇ D.130 5-Pyridimidyl H D.131 5-Pyridimidyl CH₃D.132 5-Pyridimidyl C₂H₅ D.133 5-Pyridimidyl n-C₃H₇ D.134 5-Pyridimidyli-C₃H₇ D.135 O—tert-Butyl CH₃ D.136 O—tert-Butyl CH₂CH₃ D.137 O—n-PropylCH₃ D.138 O—n-Butyl CH₃ D.139 O—CH₂C₆H₅ CH₃ D.140 2-Furyl H D.1412-Furyl CH₃ D.142 O—n-Pentyl CH₃ D.143 O—n-Hexyl CH₃ D.144 3-Furyl HD.145 3-Furyl CH₃ D.146 2-Oxazolyl H D.147 2-Oxazolyl CH₃ D.1482-Oxazolyl C₂H₅ D.149 2-Oxazolyl n-C₃H₇ D.150 2-Oxazolyl i-C₃H₇ D.1514-Oxazolyl H D.152 4-Oxazolyl CH₃ D.153 4-Oxazolyl C₂H₅ D.154 4-Oxazolyln-C₃H₇ D.155 4-Oxazolyl i-C₃H₇ D.156 3-Isoxazolyl H D.157 3-IsoxazolylCH₃ D.158 3-Isoxazolyl C₂H₅ D.159 3-Isoxazolyl n-C₃H₇ D.160 3-Isoxazolyli-C₃H₇ D.161 5-Isoxazolyl H D.162 5-Isoxazolyl CH₃ D.163 5-IsoxazolylC₂H₅ D.164 5-Isoxazolyl n-C₃H₇ D.165 5-Isoxazolyl i-C₃H₇ D.1663-Pyrazolyl H D.167 3-Pyrazolyl CH₃ D.168 3-Pyrazolyl C₂H₅ D.1693-Pyrazolyl n-C₃H₇ D.170 3-Pyrazolyl i-C₃H₇ D.171 4-Pyrazolyl H D.1724-Pyrazolyl CH₃ D.173 4-Pyrazolyl C₂H₅ D.174 4-Pyrazolyl n-C₃H₇ D.1754-Pyrazolyl i-C₃H₇

TABLE E E.1 C₆H₅ E.2 2-F—C₆H₄ E.3 3-F—C₆H₄ E.4 4-F—C₆H₄ E.5 2-Cl—C₆H₄E.6 3-Cl—C₆H₄ E.7 4-Cl—C₆H₄ E.8 2-CH₃—C₆H₄ E.9 3-CH₃—C₆H₄ E.104-CH₃—C₆H₄ E.11 2,4-(CH₃)₂—C₆H₃ E.12 2,6-(CH₃)₂—C₆H₃ E.13 2,6-F₂—C₆H₃E.14 2,6-Cl₂—C₆H₃ E.15 2,4-F₂—C₆H₃ E.16 2,4-Cl₂—C₆H₃ E.17 2,5-F₂—C₆H₃E.18 2,5-Cl₂—C₆H₃ E.19 2,5-(CH₃)₂—C₆H₃ E.20 2-OCH₃—C₆H₄ E.21 3-OCH₃—C₆H₄E.22 4-OCH₃—C₆H₄ E.23 2-CN—C₆H₄ E.24 3-CN—C₆H₄ E.25 4-CN—C₆H₄ E.262-NO₂—C₆H₄ E.27 3-NO₂—C₆H₄ E.28 4-NO₂—C₆H₄ E.29 2-CO₂CH₃—C₆H₄ E.302-COCH₃—C₆H₄ E.31 3-COCH₃—C₆H₄ E.32 4-CO₂CH₃—C₆H₄ E.33 4-COCH₃—C₆H₄ E.342-CH₃-4-COCH₃—C₆H₃ E.35 CH₃ E.36 CH₂CH₃ E.37 CH₂CH₂CH₃ E.38 iso-PropylE.39 n-Propyl E.40 tert-Butyl E.41 Hexyl E.42 Pentyl E.43 Isopropyl E.44CH(CH₂CH₃)₂ E.45 CH₂CF₃ E.46 CF₃ E.47 CHF₂ E.48 CClF₂ E.49 2-OH—C₆H₄E.50 2-NH—CONH₂—C₆H₄ E.51 2-NH—SO₂CH₃—C₆H₄ E.52 2-SCN—C₆H₄ E.533-SCN—C₆H₄ E.54 4-SCN—C₆H₄ E.55 2-SCH₃—C₆H₄ E.56 3-SCH₃—C₆H₄ E.574-SCH₃—C₆H₄ E.58 2-CHO—C₆H₄ E.59 3-CHO—C₆H₄ E.60 4-CHO—C₆H₄ E.612-CONH₂—C₆H₄ E.62 3-CONH₂—C₆H₄ E.63 4-CONH₂—C₆H₄ E.64 2-CONH(CH₃)—C₆H₄E.65 2-CONH(CH₃)—C₆H₄ E.66 4-CONH(CH₃)—C₆H₄ E.67 3-iso-Propyl—C₆H₄ E.684-iso-Propyl—C₆H₄ E.69 3-tert-Butyl—C₆H₄ E.70 4-tert-Butyl—C₆H₄

TABLE F No. R¹ R² X Y—A Data mp. (° C.); IR (cm⁻¹); NMR (ppm) F.1 CH₃CH₃ —C(CO₂CH₃)═NOCH₃ CH₃ON═C(4-F—C₆H₄)—C(CH₃)═N—O— 2.32 (s, 3H, CH₃),2.54 (s, 3H, CH₃), 2.60 (s, 3H, CH₃), 3.76 (s, 3H, OCH₃), 4.0 (s, 3H,OCH₃), 4.06 (s, 3H, OCH₃), 7.1 (m, 2H, arom.), 7.46 (m, 2H, arom.).

The compounds I are useful as fungicides.

The compounds I are distinguished by an outstanding activity against abroad spectrum of phytopathogenic fungi, in particular from the classesof the Ascomycetes and Basidiomycetes. Some of them act systemically andcan be employed as foliar and soil fungicides.

They are especially important for controlling a large number of fungi ina variety of crop plants such as wheat, rye, barley, oats, rice, corn,grass, cotton, soybeans, coffee, sugar cane, grapevines, fruit species,ornamentals and vegetable species such as cucumbers, beans andcucurbits, and on the seeds of these plants.

Specifically, they are suitable for controlling the following plantdiseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphecichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaeraleucotricha on apples, Uncinula necator on grapevines, Puccinia specieson cereals, Rhizoctonia species on cotton and lawns, Ustilago species oncereals and sugar cane, Venturia inaequalis (scab) on apples,Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytiscinerea (gray mold) on strawberries, grapevines, Cercospora arachidicolaon groundnuts, Pseudocercosporella herpotrichoides on wheat, barley,Pyricularia oryzae on rice, Phytophthora infestans on potatoes andtomatoes, Fusarium and Verticillium species on various plants,Plasmopara viticola on grapevines, Alternaria species on vegetables andfruit.

The compounds I are used by treating the fungi, or the plants, seeds,materials or the soil to be protected against fungal attack, with afungicidally effective amount of the active ingredients. Application iseffected before or after infection of the materials, plants or seeds bythe fungi.

They can be converted into the customary formulations, such assolutions, emulsions, suspensions, dusts, powders, pastes and granules.The use form depends on the respective intended purpose; in any case, itshould guarantee fine and uniform distribution of the compoundsaccording to the invention. The formulations are prepared in a knownmanner, for example by extending the active ingredient with solventsand/or carriers, if desired using emulsifiers and dispersants, it alsobeing possible to use other organic solvents as auxiliary solvents ifwater is used as the diluent. Suitable auxiliaries are essentially:

solvents such as aromatics (eg. xylene), chlorinated aromatics (eg.chlorobenzenes), paraffins (eg. petroleum fractions), alcohols (eg.methanol, butanol), ketones (eg. cyclohexanone), amines (eg.ethanolamine, dimethylformamide) and water; carriers such as groundnatural minerals (eg. kaolins, clays, talc, chalk) and ground syntheticminerals (eg. highly disperse silica, silicates); emulsifiers such asnonionic and anionic emulsifiers (eg. polyoxyethylene fatty alcoholethers, alkylsulfonates and arylsulfonates) and dispersants, such aslignosulfite waste liquors and methylcellulose.

In general, the fungicidal compositions comprise from 0.1 to 95,preferably from 0.5 to 90, % by weight of active ingredient.

Depending on the nature of the desired effect, the rates of applicationare from 0.01 to 2.0 kg of active ingredient per ha.

For seed treatment, amounts of active ingredient of from 0.001 to 0.1 g,preferably 0.01 to 0.05 g, are generally required per kilogram of seed.

In the use form as fungicides, the compositions according to theinvention can also be present together with other active ingredients,eg. with herbicides, insecticides, growth regulators, fungicides oralternatively fertilizers.

A mixture with fungicides frequently results in a widening of thefungicidal spectrum of action.

The following list of fungicides with which the compounds according tothe invention can be used are intended to illustrate the possiblecombinations, but not to restrict them:

sulfur, dithiocarbamates and their derivatives, such as iron(III)dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate,manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuramdisulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate),ammonia complex of zinc (N,N′-propylenebisdithiocarbamate), zinc(N,N′-propylenebisdithiocarbamate), N,N′-polypropylenebis(thiocarbamoyl)disulfide;

nitro derivatives such as dinitro(1-methylheptyl)phenyl crotonate,2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate,2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate, diisopropyl5-nitroisophthalate;

heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate,2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethylphthalimidophosphonothioate,5-amino-1-[bis(dimethylamino)phosphinyl]-3-3-phenyl-1,2,4-triazole,2,3-dicyano-1,4-dithioanthraquinone,2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl1-(butylcarbamoyl)-2-benzimidazolecarbamate,2-methoxycarbonylaminobenzimidazole, 2-(furyl-(2))benzimidazole,2-(thiazolyl-(4))benzimidazole,N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,N-trichloromethylthiotetrahydrophthalimide,N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenylsulfamide,5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole,2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene,4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,2-thiopyridine-1-oxide, 8-hydroxyquinoline and its copper salt,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin 4,4-dioxide,2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide,2,4,5-trimethylfuran-3-carboxanilide,N-cyclohexyl-2,5-dimethylfuran-3-carboxamide,N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,2-methylbenzanilide, 2-iodobenzanilide,N-2,2,2-trichloro-1-(4-morpholinyl)-ethylformamide,piperazine-1,4-diylbis(1-(2,2,2-trichloroethyl)formamide,1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,2,6-dimethyl-N-tridecylmorpholine and its salts,2,6-dimethyl-N-cyclododecylmorpholine and its salts,N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethyl-morpholine,N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine,1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N′-imidazolylurea,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,bis(p-chlorophenyl)-3-pyridinemethanol,1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene,1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,

and a variety of fungicides such as dodecylguanidine acetate,3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide,hexachlorobenzene,

DL-methyl N-(2,6-dimethylphenyl)-N-furoyl(2)-alaninate, DL-methylN-(2,6-dimethylphenyl)-N-(2′-methoxyacetyl)alaninate,N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone,DL-methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate,5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide,1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole,2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol,N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,1-((bis(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

The compounds of the formula I are furthermore useful for controllingpests from the classes of the insects, arachnids and nematodes. They canbe employed as pesticides in crop protection, and in the hygiene,stored-product and veterinary sector.

The harmful insects include, from the order of the lepidopterans(Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabamaargillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographagamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana,Cheimatobia brumata, Choristoneura fumiferana, Choristoneuraoccidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini,Diaphania nitidalis, Diatraea grandiosella, Earias insulana,Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana,Feltia subterranea, Galleria mellonella, Grapholitha funebrana,Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothiszea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeutamalinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygmaexigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletisblancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar,Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestrabrassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea,Pectinophora gossypiella, Peridroma saucia, Phalera bucephala,Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae,Plathypena scabra, Plutella xylostella, Pseudoplusia includens,Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella,Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis,Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana,Trichoplusia ni, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example, Agrilussinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallussolstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum,Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchusrufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassidanebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis,Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus,Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata,Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis,Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis,Hypera postica, Ips typographus, Lema bilineata, Lema melanopus,Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrusoryzophilus, Melanotus communis, Meligethes aeneus, Melolonthahippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchussulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotretachrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotretanemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus,Sitophilus granaria.

From the order of the dipterans (Diptera), for example, Aedes aegypti,Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitiscapitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomyamacellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culexpipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fanniacanicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobiairritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata,Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina,Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Muscadomestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomyahysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata,Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipulaoleracea, Tipula paludosa.

From the order of the thrips (Thysanoptera), for example, Frankliniellafusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothripscitri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenopterans (Hymenoptera), for example, Athaliarosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta,Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata,Solenopsis invicta.

From the order of the heteropterans (Heteroptera), for example,Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercuscingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistusimpictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lyguspratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyantaperditor.

From the order of the homopterans (Homoptera), for example,Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphisfabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicorynebrassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusiapiceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae,Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megouraviciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi,Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida,Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus,Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphisgraminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteusvitifolii.

From the order of the termites (Isoptera), for example, Calotermesflavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termesnatalensis.

From the order of the orthopterans (Orthoptera), for example, Achetadomestica, Blatta orientalis, Blattella germanica, Forficulaauricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplusbivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplussanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplanetaamericana, Schistocerca americana, Schistocerca peregrina, Stauronotusmaroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example, arachnids (Acarina) suchas Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilusannulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpusphoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychuscarpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodesrubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychuspilosus, Dermanyssus gallinae, Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus,Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus,Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius,Tetranychus urticae.

From the class of the nematodes, for example, root gall nematodes, eg.Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica,cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae,Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stem andleaf eelworms, eg. Belonolaimus longicaudatus, Ditylenchus destructor,Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidoruselongatus, Radopholus similis, Rotylenchus robustus, Trichodorusprimitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius,Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus,Pratylenchus goodeyi.

The active ingredients can be applied as such, in the form of theirformulations or the use forms prepared therefrom, eg. in the form ofdirectly sprayable solutions, powders, suspensions or dispersions,emulsions, oil dispersions, pastes, dusts, materials for spreading, andgranules, by means of spraying, atomizing, dusting, spreading orpouring. The use forms depend entirely on the intended purposes; in anycase, they should guarantee the finest possible distribution of theactive ingredients according to the invention.

The concentrations of active ingredient in the ready-to-use preparationscan vary within substantial ranges.

In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active ingredients can also be employed very successfully in theultra-low-volume method (ULV), it being possible to apply formulationscomprising more than 95% by weight of active ingredient, or even theactive ingredient without additives.

Under field conditions, the rate of active ingredient to be applied forcontrolling pests is from 0.1 to 2.0, preferably 0.2 to 1.0, kg/ha.

Substances which are suitable for preparing directly sprayablesolutions, emulsions, pastes or oil dispersions are mineral oilfractions of medium to high boiling point, such as kerosene or dieseloil, furthermore coal tar oils, and oils of vegetable or animal origin,aliphatic, cyclic or aromatic hydrocarbons, eg. benzene, toluene,xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or theirderivatives, methanol, ethanol, propanol, butanol, chloroform, carbontetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone,strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide,N-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (sprayable powders, oil dispersions) by adding water.To prepare emulsions, pastes or oil dispersions, the substances, as suchor dissolved in an oil or solvent, can be homogenized in water by meansof wetting agent, adhesive, dispersant or emulsifier. Alternatively, itis possible to prepare concentrates from active substance, wettingagent, adhesive, dispersant or emulsifier and, if desired, solvent oroil, which are suitable for dilution with water.

Suitable surfactants are alkali metal, alkaline earth metal and ammoniumsalts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonicacid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates,alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acidsand their alkali metal and alkaline earth metal salts, salts of sulfatedfatty alcohol glycol ether, condensates of sulfonated naphthalene andnaphthalene derivatives with formaldehyde, condensates of naphthalene orof naphthalenesulfonic acid with phenol and formaldehyde,polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol,octylphenyl, nonylphenol, alkylphenol polyglycol ether, tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, laurylalcohol polyglycol ether acetal, sorbitol ester, lignosulfite wasteliquors and methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orconcomitantly grinding the active substances with a solid carrier.

In general, the formulations comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active ingredient. Theactive ingredients are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to NMR spectrum).

Examples of formulations are:

I. 5 parts by weight of a compound according to the invention are mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dust which comprises 5% by weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention aremixed intimately with a mixture of 92 parts by weight of pulverulentsilica gel and 8 parts by weight of paraffin oil, which have beensprayed onto the surface of this silica gel. This gives a preparation ofthe active ingredient with good adhesion properties (comprises 23% byweight of active ingredient).

III. 10 parts by weight of a compound according to the invention aredissolved in a mixture composed of 90 parts by weight of xylene, 6 partsby weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol ofoleic acid N-monoethanolamide, 2 parts by weight of calciumdodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol ofethylene oxide to 1 mol of castor oil (comprises 9% by weight of activeingredient).

IV. 20 parts by weight of a compound according to the invention aredissolved in a mixture composed of 60 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts by weightof the adduct of 40 mol of ethylene oxide to 1 mol of castor oil(comprises 16% by weight of active ingredient).

V. 80 parts by weight of a compound according to the invention are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 7 parts byweight of pulverulent silica gel, and the mixture is ground in a hammermill (comprises 80% by weight of active ingredient).

VI. 90 parts by weight of a compound according to the invention aremixed with 10 parts by weight of N-methyl-α-pyrrolidone, and this givesa solution which is useful for use in the form of microdrops (comprises90% by weight of active ingredient).

VII. 20 parts by weight of a compound according to the invention aredissolved in a mixture composed of 40 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weightof the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.Pouring the solution into 100,000 parts by weight of water and finelydistributing it therein gives an aqueous dispersion which comprises0.02% by weight of the active ingredient.

VIII.20 parts by weight of a compound according to the invention aremixed thoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium saltof a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel and the mixture is ground in a hammermill. Finely distributing the mixture in 20,000 parts by weight of watergives a spray mixture which comprises 0.1% by weight of the activeingredient.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Examples of solid carriers are mineral earths such as silicas,silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk,bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,magnesium sulfate, magnesium oxide, ground synthetic materials,fertilizers, eg. ammonium sulfate, ammonium phosphate, ammonium nitrate,ureas and products of vegetable origin such as cereal meal, tree barkmeal, wood meal and nutshell meal, cellulose powders and other solidcarriers.

Various types of oils, or herbicides, fungicides, other pesticides, andbactericides, can be added to the active ingredients, if appropriatealso just before use (tank mix). These agents can be admixed with theagents according to the invention in a weight ratio of 1:10 to 10:1.

SYNTHESIS EXAMPLES EXAMPLE 1

2 g (10.2 mmol) of methyl α-(4-chloro-6-methyl-5-pyrimidinyl)-acetate(for preparation cf. EP 634 405-A1) are stirred at 45° C. for 10 hourstogether with 2.0 g of potassium tert-butoxide and 1 g (10.2 mmol) ofdiacetyl monooxime in 80 ml of dimethylformamide. The mixture is thenhydrolyzed with dil. hydrochloric acid, extracted with methyl tert-butylether (MtBE), and the combined org. phases are washed with water, driedand concentrated. The residue is treated with 60 ml of warm methanol, 1g of O-methylhydroxylamine hydrochloride and 0.6 g of dry molecularsieve beads (3 Å) and the mixture is stirred at room temperature forfour days. The solution is then filtered off, concentrated andpartitioned between MtBE and water, and the organic phases are washedwith water, dried and concentrated.

1.3 g of the title compound remain, which is employed without furtherpurification in Example 2.

Example 2

1.2 g (4 mmol) of the compound 1 from Example 1 are added at −40° C. tothe solution from 1.95 g (16 mmol) of potassium tert-butoxide in 150 mlof dimethoxyethane. After 1 h, 15 ml ofdimethylformamide-dimethylsulfate (1:1 adduct) are added, and themixture is allowed to come to room temperature and is extracted withMtBE. The organic phases are washed with saturated sodium chloridesolution, dried and concentrated. The residue is taken up in 50 ml ofdiethyl ether, treated with 0.5 g of p-toluenesulfonic acid and 3 ml ofwater and the mixture is subsequently stirred at room temperature fortwo days. It is then neutralized with solid sodium bicarbonate,extracted with ether, dried and concentrated again. The residue is takenup without further purification in 80 ml of dimethylformamide (DMF) andtreated with cooling with 0.55 g (4 mol) of K₂CO₃ and 0.5 g (4 mmol) ofdimethyl sulfate. The mixture is then stirred at room temperature for 3h, extracted with MtBE, and the org. phases are dried over sodiumsulfate and concentrated. The residue is chromatographed on silica gelusing n-heptane/ethyl acetate (1:1) as an eluent. 0.7 g of the titlecompound 2 remains as a resin.

¹H-NMR (CDCl₃): 2.43 (s,3H); 3.74 (s,3H); 3.9 (3,H).

Examples of action against harmful fungi

It was possible to show the fungicidal action of the compounds of theformula I by the following tests:

Use Example 1—Activity against Plasmopara viticola

Leaves of potted vines of the Müller-Thurgau variety were sprayed withaqueous active compound preparation, which was prepared using a stocksolution of 10% active compound, 63% cyclohexanone and 27% emulsifier,until dripping wet. In order to be able to assess the long-term effectof the substances, the plants were placed in a greenhouse for 7 daysafter the spray coating had dried on. Only then were the leavesinoculated with an aqueous zoospore suspension of Plasmopara viticola.The vines were then placed first for 48 hours in a water vapor-saturatedchamber at 24° C. and then for 5 days in a greenhouse at from 20 to 30°C. After this time, the plants were again placed in a moist chamber for16 hours to accelerate sporangiophore escape. The extent of thedevelopment of attack on the undersides of the leaves was thendetermined visually.

% attack on the leaves after application of aqueous active compoundpreparation containing Active compound 250 ppm Table F, No. F.1 15Untreated 70

Examples of action against animal pests

It was possible to show the action of the compounds of the generalformula I against animal pests by the following tests:

The active compounds were prepared

a) as a 0.1% strength solution in acetone or

b) as a 10% strength emulsion in a mixture of 70% by weight ofcyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wettingagent having emulsifying and dispersant action based on ethoxylatedalkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL, emulsifierbased on ethoxylated fatty alcohols)

and accordingly diluted to the desired concentration with acetone in thecase of a) or with water in the case of b).

After conclusion of the tests, the lowest concentration in each case wasdetermined at which the compounds still caused an 80-100% inhibition ormortality in comparison with untreated control tests (action thresholdor minimum concentration).

We claim:
 1. A pyrimidine compound I

wherein X is C(CO₂CH₃)═NOCH₃, C(CONHCH₃)═NOCH₃, C(CO₂CH₃)═CHOCH₃,C(CO₂CH₃)═CHCH₃ or N(CO₂CH₃)—OCH₃; R¹ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxy; R² is hydrogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl; A is

wherein the bond marked * is to Y; R³ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, phenoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, cyano,C₁-C₄-alkoxy, hydroxyl or halogen; R⁴ is hydrogen, C₁-C₈-alkyl,C₁-C₄-haloalkyl, C₁-C₆-cyanoalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₂-C₄-alkenyloxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,C₁-C₄-oxoalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkenyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl orC₁-C₄-alkoxy; Y is hydrogen, hydroxyl, halogen, unsubstituted orsubstituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl,alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio,hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio, and or a saltthereof.
 2. A pyrimidine compound I

wherein X is C(CO₂CH₃)═NOCH₃, C(CONHCH₃)═NOCH₃, C(CO₂CH₃)═CHOCH₃,C(CO₂CH₃)═CHCH₃ or N(CO₂CH₃)—OCH₃; R¹ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxy; R² is hydrogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl; A is

wherein the bond marked * is to Y; R³ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, phenoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, cyano,C₁-C₄-alkoxy, hydroxyl or halogen; R⁴ is hydrogen, C₁-C₈-alkyl,C₁-C₄-haloalkyl, C₁-C₆-cyanoalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₂-C₄-alkenyloxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,C₁-C₄-oxoalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkenyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl orC₁-C₄-alkoxy; Y is hydrogen, hydroxyl, halogen, C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy, C₁-C₄-alkylthio,C₃-C₆-cycloalkyl, C₅-C₈-cycloalkenyl, heterocyclyl, aryl, aryloxy,arylthio, aryl-C₁-C₄-alkyl, aryl-C₂-C₄-alkenyl, aryloxy-C₁-C₄-alkyl,aryl-C₁-C₄-alkoxy, hetaryl, hetaryloxy, hetarylthio,hetaryl-C₁-C₄-alkyl, hetarylthio-C₁-C₄-alkyl, hetaryl-C₁-C₄-alkoxy orhetaryl-C₂-C₄-alkenyl, wherein the cyclic radicals are unsubstituted orpartially or completely halogenated and/or carry 1 to 3 of the followinggroups: cyano, nitro, hydroxyl, mercapto, amino, formyl, carboxyl,aminocarbonyl, aminothiocarbonyl, C₁-C₁ ₂-alkyl, C₁-C₆-haloalkyl,C₁-C₆-hydroxyalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylcarbonyl,C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyl, benzyloxycarbonyl,C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl,C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl,C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C(═NOR^(b))—Z_(n)—R^(c),NR^(f)—CO—D—R⁹, benzyl, benzyloxy, aryl, aryloxy, hetaryl or hetaryloxy,wherein the last 6 mentioned radicals are unsubstituted or partially orcompletely halogenated and/or carry 1 to 3 of the following groups:cyano, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₁-C₄-alkoxy, nitro,C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkyl, hydroxyl, rhodano, formyl,aminocarbonylamino, methylsulfonylamino, aminocarbonyl andC₁-C₆-alkylaminocarbonyl; Z is oxygen, sulfur or nitrogen, the nitrogenbearing hydrogen or C₁-C₆-alkyl; D is a direct bond, oxygen or NR^(h); nis 0 or 1; R^(b) and R^(c) independently of one another are hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or benzyl; R^(f) is hydrogen,hydroxyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₆-alkoxy or C₁-C₆-alkoxycarbonyl; R^(g) and R^(h)independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, aryl,aryl-C₁-C₆-alkyl, hetaryl or hetaryl-C₁-C₆-alkyl, R⁹ is hydrogen orC₁-C₆-alkyl; or a salt thereof.
 3. The compound I defined in claim 1,wherein R¹ is methyl and R² is hydrogen.
 4. The compound I defined inclaim 1, wherein R¹ is hydrogen and R² is methyl.
 5. The compound Idefined in claim 1, wherein R¹ is trifluoromethyl and R² is hydrogen. 6.The compound I defined in claim 1, wherein R¹ is hydrogen and R² istrifluoromethyl.
 7. The compound I defined in claim 1, wherein R¹ and R²are hydrogen.
 8. The compound I defined in claim 2, wherein R¹ is methyland R² is hydrogen.
 9. The compound I defined in claim 2, wherein R¹ ishydrogen and R² is methyl.
 10. The compound I defined in claim 2,wherein R¹ is trifluoromethyl and R² is hydrogen.
 11. The compound Idefined in claim 2, wherein R¹ is hydrogen and R² is trifluoromethyl.12. The compound I defined in claim 2, wherein R¹ and R² are hydrogen.13. A pyrimidine compound of the formula

wherein X′ is C(═O)—CO₂CH₃, NO₂, NH—OH or N(OH)—CO₂CH₃; R¹ is hydrogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxy; R² is hydrogen,C₁-C₄-alkyl or C₁-C₄-haloalkyl; A is

wherein the bond marked * is to Y; R³ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, phenoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, cyano,C₁-C₄-alkoxy, hydroxyl or halogen; R⁴ is hydrogen, C₁-C₈-alkyl,C₁-C₄-haloalkyl, C₁-C₆-cyanoalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₂-C₄-alkenyloxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,C₁-C₄-oxoalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkenyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl orC₁-C₄-alkoxy; Y is hydrogen, hydroxyl, halogen, unsubstituted orsubstituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl,alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio,hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio.
 14. A pyrimidinecompound of the formula

wherein X′ is C(═O)—CO₂CH₃, NO₂, NH—OH or N(OH)—CO₂CH₃; R¹ is hydrogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxy; R² is hydrogen,C₁-C₄-alkyl or C₁-C₄-haloalkyl; A is

wherein the bond marked * is to Y; R³ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, phenoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, cyano,C₁-C₄-alkoxy, hydroxyl or halogen; R⁴ is hydrogen, C₁-C₈-alkyl,C₁-C₄-haloalkyl, C₁-C₆-cyanoalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₂-C₄-alkenyloxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,C₁-C₄-oxoalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkenyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl orC₁-C₄-alkoxy; Y is hydrogen, hydroxyl, halogen, C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkoxy, C₁-C₄-alkylthio,C₃-C₆-cycloalkyl, C₅-C₈-cycloalkenyl, heterocyclyl, aryl, aryloxy,arylthio, aryl-C₁-C₄-alkyl, aryl-C₂-C₄-alkenyl, aryloxy-C₁-C₄-alkyl,aryl-C₁-C₄-alkoxy, hetaryl, hetaryloxy, hetarylthio,hetaryl-C₁-C₄-alkyl, hetarylthio-C₁-C₄-alkyl, hetaryl-C₁-C₄-alkoxy orhetaryl-C₂-C₄-alkenyl, wherein the cyclic radicals are unsubstituted orpartially or completely halogenated and/or carry 1 to 3 of the followinggroups: cyano, nitro, hydroxyl, mercapto, amino, formyl, carboxyl,aminocarbonyl, aminothiocarbonyl, C₁-C₁₂-alkyl, C₁-C₆-haloalkyl,C₁-C₆-hydroxyalkyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylcarbonyl,C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxycarbonyl, benzyloxycarbonyl,C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,C₁-C₆-alkylaminocarbonyl, di-C₁-C₆-alkylaminocarbonyl,C₁-C₆-alkylaminothiocarbonyl, di-C₁-C₆-alkylaminothiocarbonyl,C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C(═NOR^(b))—Z_(n)—R^(c),NR^(f)—CO—D—R⁹, benzyl, benzyloxy, aryl, aryloxy, hetaryl or hetaryloxy,wherein the last 6 mentioned radicals are unsubstituted or partially orcompletely halogenated and/or carry 1 to 3 of the following groups:cyano, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₁-C₄-alkoxy, nitro,C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkyl, hydroxyl, rhodano, formyl,aminocarbonylamino, methylsulfonylamino, aminocarbonyl andC₁-C₆-alkylaminocarbonyl; Z is oxygen, sulfur or nitrogen, the nitrogenbearing hydrogen or C₁-C₆-alkyl; D is a direct bond, oxygen or NR^(h); nis 0 or 1; R^(b) and R^(c) independently of one another are hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or benzyl; R^(f) is hydrogen,hydroxyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₆-alkoxy or C₁-C₆-alkoxycarbonyl; R^(g) and R^(h)independently of one another are hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, aryl,aryl-C₁-C₆-alkyl, hetaryl or hetaryl-C₁-C₆-alkyl, and R⁹ is hydrogen orC₁-C₆-alkyl.
 15. The pyrimidine compound defined in claim 14, wherein X′is C(═O)—CO₂CH₃.
 16. The pyrimidine compound defined in claim 14,wherein X′ is NO₂, NH—OH or N(OH)—CO₂CH₃.
 17. The pyrimidine compounddefined in claim 14, wherein R¹ is methyl and R² is hydrogen.
 18. Thepyrimidine compound defined in claim 14, wherein R¹ is hydrogen and R²is methyl.
 19. The pyrimidine compound defined in claim 14, wherein R¹is trifluoromethyl and R² is hydrogen.
 20. The pyrimidine compounddefined in claim 14, wherein R¹ is hydrogen and R² is trifluoromethyl.21. The pyrimidine compound defined in claim 14, wherein R¹ and R² arehydrogen.
 22. A process for preparing a compound I

wherein X is C(CO₂CH₃)═NOCH₃, R¹ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxy; R² is hydrogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl; A is

wherein the bond marked * is to Y; R³ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, phenoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, cyano,C₁-C₄-alkoxy, hydroxyl or halogen; R⁴ is hydrogen, C₁-C₈-alkyl,C₁-C₄-haloalkyl, C₁-C₆-cyanoalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₂-C₄-alkenyloxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,C₁-C₄-oxoalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkenyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl orC₁-C₄-alkoxy; Y is hydrogen, hydroxyl, halogen, unsubstituted orsubstituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl,alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio,hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio, which comprisesreacting an α-oxopyrimidinylacetic acid IIa

with methoxyamine or methoxyamine hydrohalide.
 23. A process forpreparing a compound I

wherein X is C(CONHCH₃)═NOCH₃, R¹ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-alkoxy; R² is hydrogen, C₁-C₄-alkyl orC₁-C₄-haloalkyl; A is

wherein the bond marked * is to Y; R³ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, phenoxy-C₁-C₄-alkyl, C₃-C₆cycloalkyl, cyano,C₁-C₄-alkoxy, hydroxyl or halogen; R⁴ is hydrogen, C₁-C₈-alkyl,C₁-C₄-haloalkyl, C₁-C₆-cyanoalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₂-C₄-alkenyloxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,C₁-C₄-oxoalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkenyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl orC₁-C₄-alkoxy; Y is hydrogen, hydroxyl, halogen, unsubstituted orsubstituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl,alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio,hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio, which comprisesreacting a 2-oximinopyrimidinylacetic acid IIb

with methylamine.
 24. A process for preparing a compound I

wherein X is C(CO₂CH₃)═CHOCH₃ or C(CO₂CH₃)═CHCH₃, R¹ is hydrogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-alkoxy; R² is hydrogen,C₁-C₄-alkyl or C₁-C₄-haloalkyl; A is

wherein the bond marked * is to Y; R³ is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, phenoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, cyano,C₁-C₄-alkoxy, hydroxyl or halogen; R⁴ is hydrogen, C₁-C₈-alkyl,C₁-C₄-haloalkyl, C₁-C₆-cyanoalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₂-C₄-alkenyloxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkylC₁-C₄-oxoalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkenyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl C₃-C₆-cycloalkyl-C₁-C₄-alkyl orC₁-C₄-alkoxy; Y is hydrogen, hydroxyl, halogen, unsubstituted orsubstituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl,alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio,hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio, and wherein A isnot —O— when X is C(CO₂CH₃)═CHOCH₃, which comprises reacting anα-oxopyrimidinylacetic acid IIa

with a Wittig reagent IIc or IId

wherein Ph is phenyl and Hal is iodine, bromine, chlorine or fluorine.25. A composition suitable for controlling animal pests or harmfulfungi, comprising a compound I as defined in claim 1 or a salt thereofand at least one formulation auxiliary.
 26. The composition defined inclaim 22 wherein the animal pest is of the insects, arachnids ornematodes class.
 27. A composition suitable for controlling animal pestsor harmful fungi, comprising a compound I as defined in claim 2 or asalt thereof and at least one formulation auxiliary.
 28. A method forcontrolling animal pests or harmful fungi, which comprises treating thepests or harmful fungi, their habitat or the plants, areas, materials orspaces to be kept free from them with an effective amount of a compoundI as defined in claim 1 or a salt thereof.
 29. A method for controllinganimal pests or harmful fungi, which comprises treating the pests orharmful fungi, their habitat or the plants, areas, materials or spacesto be kept free from them with an effective amount of a compound I asdefined in claim 2 or a salt thereof.